Triethylamine → 4-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-(methylsulfonyl)piperidine-4-carboxamide

HRID 1867726Notes

Reaction equation

HRID 1867726 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[Cl:7][C:8]1[C:9]([F:39])=[C:10]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:37][CH3:38])=[C:22]([CH2:25][N:26]([CH3:36])[C:27]4([C:33]([NH2:35])=[O:34])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH:23]=3)[N:18]=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C>ClCCl>[Cl:7][C:8]1[C:9]([F:39])=[C:10]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:37][CH3:38])=[C:22]([CH2:25][N:26]([CH3:36])[C:27]4([C:33]([NH2:35])=[O:34])[CH2:32][CH2:31][N:30]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:29][CH2:28]4)[CH:23]=3)[N:18]=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 690487244-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxamide hydrochloride

Product 1

HCID 579798374-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-(methylsulfonyl)piperidine-4-carboxamideYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (7.5 μl, 0.094 mmol) was added to a stirred solution of 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxamide hydrochloride (0.05 g, 0.085 mmol) and triethylamine (53 μl, 0.38 mmol) in dichloromethane (1 ml) at room temperature. The reaction mixture was stirred at room temperature for 1 hour, concentrated and purified by preparative LCMS (standard basic system) to give the title product (0.0107 g, 23%) as a white solid; 1H NMR Spectrum: (DMSO-d6) 1.98 (m, 2H), 2.22 (m, 2H), 2.36 (s, 3H), 2.84 (s, 3H), 2.96 (m, 2H), 3.44 (m, 2H), 3.66 (s, 2H), 3.98 (s, 3H), 7.19 (s, 1H), 7.26-7.30 (m, 3H), 7.52-7.53 (m, 2H), 8.33 (s, 1H), 8.42 (s, 1H), 9.70 (s, 1H); Mass Spectrum: (M+H)+ 551.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS (standard basic system)

Sources & evidence

ORD record
ord-4adbe0937d9b4d6592fb71c3ca669da0
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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