HCID 15752298, compound → HCID 135674998, compound

HRID 1198200Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7](COC(=O)C(C)(C)C)[C:8]([CH3:12])=[N:9]2)=[CH:4][C:3]=1[CH2:22][N:23]([C:27]1[CH:46]=[CH:45][C:30]([C:31](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:32])=[CH:29][CH:28]=1)[CH2:24][C:25]#[CH:26].[NH2:47][CH:48]([C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([N+:57]([O-:59])=[O:58])[CH:52]=1)[CH2:49][OH:50]>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[NH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][C:3]=1[CH2:22][N:23]([C:27]1[CH:28]=[CH:29][C:30]([C:31]([NH:47][CH:48]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([N+:57]([O-:59])=[O:58])[CH:52]=2)[CH2:49][OH:50])=[O:32])=[CH:45][CH:46]=1)[CH2:24][C:25]#[CH:26]

Participants

Reactant 2

HCID 15752298HCID 15752298, compound

HCID 157522992-Amino-2-(3-nitrophenyl)ethan-1-ol

Product 1

HCID 135674998HCID 135674998, compoundYield 61%

Procedure

Using an analogous procedure to that described in Example 19, pentafluorophenyl p-[N-(7-bromo-2-methyl-4-oxo-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzoate was reacted with 2-amino-2-(3-nitrophenyl)ethanol and the pivaloyloxymethyl protecting group was removed from the resultant product to give p-[N-(7-bromo-2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]-N-[2-hydroxy-1-(3-nitrophenyl)ethyl]benzamide (containing 0.25 equivalents of water) in 61% yield, m.p. 221°-232° C.

Workup

customthe pivaloyloxymethyl protecting group was removed from the resultant product

Sources & evidence

ORD record: ord-fa60e5021c38493b88d44a457e71c396
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05280027

Reaction notes

Loading…