Methanesulfonyl chloride → N-(2-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)ethyl)methanesulfonamide

HRID 595315Notes

Reaction equation

HRID 595315 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][S:11](Cl)(=[O:13])=[O:12].Cl.[NH2:16][CH2:17][CH2:18][N:19]1[CH:23]=[C:22]([C:24]2[CH:25]=[C:26]([NH:31][C:32]3[N:37]=[C:36]([CH:38]([F:40])[F:39])[CH:35]=[CH:34][N:33]=3)[CH:27]=[C:28]([CH3:30])[CH:29]=2)[CH:21]=[N:20]1>ClCCl>[F:40][CH:38]([F:39])[C:36]1[CH:35]=[CH:34][N:33]=[C:32]([NH:31][C:26]2[CH:25]=[C:24]([C:22]3[CH:21]=[N:20][N:19]([CH2:18][CH2:17][NH:16][S:11]([CH3:10])(=[O:13])=[O:12])[CH:23]=3)[CH:29]=[C:28]([CH3:30])[CH:27]=2)[N:37]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 118208517N-(3-(1-(2-amino ethyl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine hydrochloride

Product 1

HCID 118208859N-(2-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)ethyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (1 mL), N,N-diisopropylethylamine (0.087 mL, 0.50 mmol) and methanesulfonyl chloride (0.023 g, 0.20 mmol) were added to a vial containing N-(3-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine hydrochloride (0.038 g, 0.10 mmol). The reaction mixture was stirred for two hours and then concentrated under reduced pressure. The residue was purified by reverse phase chromatography (acetonitrile/water with 0.1% TFA modifier) to afford N-(2-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)ethyl)methanesulfonamide. MS ESI calc'd. for C15H21F2N6O2S [M+H]+ 423. found 423. 1H NMR (600 MHz, DMSO-d6): δ 9.80 (s, 1H), 8.64 (d, J=4.9 Hz, 1H), 8.02 (s, 1H), 7.78 (d, J=5.5 Hz, 2H), 7.31 (s, 1H), 7.19 (t, J=5.9 Hz, 1H), 7.01 (d, J=6.7 Hz, 2H), 6.81 (t, J=54.5 Hz, 1H), 4.18 (t, J=6.2 Hz, 2H), 3.36-3.35 (m, 2H), 2.77 (s, 3H), 2.25 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by reverse phase chromatography (acetonitrile/water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-79db059f8ff042ed8db0c8ae4ef7d1f5
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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