Methylamine → HCID 66763032, compound

HRID 578697Notes

Reaction equation

HRID 578697 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH:19]=1.CS(Cl)(=O)=O.[CH3:40][NH2:41]>COCCOC>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]([NH:24][C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=2)[CH2:17][NH:16][C:6]2[C:5]3[C:10](=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=[C:3]([CH2:2][NH:41][CH3:40])[CH:4]=3)[N:9]=[CH:8][N:7]=2)=[O:34])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 31297Methanesulfonyl chlorideHCID 66763153HCID 66763153, compound

Product 1

HCID 66763032HCID 66763032, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 6-(hydroxymethyl)-4-({3-[(4-methoxybenzoyl)amino]benzyl}amino)quinazoline-8-carboxamide (12.40 mg; 0.03 mmol; 1.00 eq.) in 1,2-dimethoxyethane (1.00 ml) added methanesulfonyl chloride (0.00 ml; 0.04 mmol; 1.50 eq.) (1.0M solution) at 0° C., stirred for 30 min, then added methyl amine (0.07 ml; 2.00 M; 0.14 mmol; 5.00 eq.) and the reaction mixture was stirred at RT overnight. Purified by HPLC to collect the desired product. MS (M+1) 471.

Workup

  1. customPurified by HPLC
  2. customto collect the desired product

Sources & evidence

ORD record
ord-e490b89b3523430d9d34c735040fadeb
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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