What document must be prepared by an issuer when selling restricted securities under Rule 144A?

When an issuer is selling restricted securities under Rule 144A, the appropriate document that must be prepared is a private placement memorandum. This document serves as a comprehensive disclosure document that provides potential investors with detailed information about the investment, including the nature of the securities being offered, the issuer's financial condition, and the associated risks.

Rule 144A facilitates the resale of restricted securities to qualified institutional buyers (QIBs) without having to register the securities with the Securities and Exchange Commission (SEC). As part of this exemption, issuers typically prepare a private placement memorandum to ensure transparency and provide the necessary information to QIBs to make informed investment decisions.

The other choices do not align with the requirements of Rule 144A in the context of selling restricted securities. A prospectus is typically used in registered offerings, while an offering circular and registration statement pertain to different regulatory contexts and do not directly apply to the sale of restricted securities under Rule 144A.