Methanesulfonyl chloride → HCID 57833261, compound

HRID 729969Notes

Reaction equation

HRID 729969 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[CH:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]=[C:24]([NH2:34])[N:23]=3)=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[NH2:34][C:24]1[N:23]=[C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:13]=3)=[CH:16][CH:17]=2)[CH:27]=[C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:25]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57833404HCID 57833404, compound

Product 1

HCID 57833261HCID 57833261, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.040 mL, 0.52 mmol) was added to a solution of N4-(4-{[2-(aminomethyl)pyridin-4-yl]oxy}phenyl)-6-phenylpyrimidine-2,4-diamine (Example 39, 0.20 g, 0.52 mmol) and DMAP (0.064 g, 0.52 mmol) in pyridine (8.0 mL) at 0° C. The mixture was allowed to warm to rt and was stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in DMF and purified by prep-HPLC to provide 82 mg of an off-white solid (27%). 1H NMR (CD3OD) δ ppm 8.57 (1H, d, J=6.8 Hz), 8.00 (2H, s), 7.77-7.80 (2H, m), 7.63 (3H, d, J=7.4 Hz), 7.42 (1H, d, J=2.5 Hz), 7.29-7.33 (3H, m), 6.58 (1H, s), 4.54 (2H, s), 3.04 (3H, s); MS ES 463 (M+H)+, calcd 463, RT=1.17 min.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-80a7977fe9a4448fb6403e953cad2d8e
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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