p-Anisoyl chloride → HCID 66763153, compound

HRID 578691Notes

Reaction equation

HRID 578691 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:20]([NH2:22])=[O:21])[CH:14]=[C:15]([CH2:18][OH:19])[CH:16]=2)[N:11]=[CH:10][N:9]=1.C(N(C(C)C)C(C)C)C.[CH3:35][O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1>C(Cl)Cl>[OH:19][CH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([C:20]([NH2:22])=[O:21])[CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:7][CH2:6][C:5]1[CH:23]=[CH:24][CH:25]=[C:3]([NH:2][C:41](=[O:42])[C:40]2[CH:44]=[CH:45][C:37]([O:36][CH3:35])=[CH:38][CH:39]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 66762569HCID 66762569, compound

Product 1

HCID 66763153HCID 66763153, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction mixture of 4-[(3-aminobenzyl)amino]-6-(hydroxymethyl)quinazoline-8-carboxamide hydrochloride (20 mg; 0.06 mmol; 1.00 eq.) and N-ethyl-N-isopropylpropan-2-amine (0.03 ml; 0.17 mmol; 3.00 eq.) in DCM was added 4-methoxybenzoyl chloride (11 mg; 0.06 mmol; 1.10 eq.). The reaction mixture was stirred at RT for 1 hr. Purified by HPLC, to get the title compound (18 mg, yield 71%) MS (M+1) 458.

Workup

  1. customPurified by HPLC

Sources & evidence

ORD record
ord-ea5539b191414997a1fec72a4cd38b0a
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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