Methanesulfonyl chloride → HCID 70656937, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([Cl:26])[CH:19]=3)=[N:14]2)=[O:9])[CH:4]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[Cl:26][C:20]1[CH:19]=[C:18]([C:15]2[CH:16]=[CH:17][N:13]([CH2:12][C@@H:11]([NH:10][C:8]([C:5]3[CH:4]=[C:3]([CH2:2][NH:1][S:29]([CH3:28])(=[O:31])=[O:30])[O:7][N:6]=3)=[O:9])[CH3:27])[N:14]=2)[CH:23]=[CH:22][C:21]=1[C:24]#[N:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-5-(aminomethyl)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)isoxazole-3-carboxamide (25 mg, 0.065 mmol) and DCM were added to a flask and stirred under nitrogen atmosphere. Methanesulfonyl chloride (9.05 μl, 0.065 mmol) was added and the reaction mixture was stirred at RT for 1 h. Methanesulfonyl chloride (6 μl) was added and the reaction mixture was stirred at RT overnight. Methanesulfonyl chloride (16 μl) was added and the reaction mixture was stirred at RT for 3 days. The reaction mixture was evaporated to dryness and the product was triturated using acetonitrile. Yield 8.3%. 1H-NMR (400 MHz; DMSO): δ 1.16 (d, 3H), 2.94 (s, 3H), 4.26-4.53 (m, 5H), 6.64 (s, 1H), 6.94 (d, 1H), 7.82 (d, 1H), 7.86 (m, 1H), 7.92 (dd, 1H), 7.98 (d, 1H), 8.09 (d, 1H), 8.81 (d, 1H)
Workup
- stirringthe reaction mixture was stirred at RT for 1 h
- stirringthe reaction mixture was stirred at RT overnight
- stirringthe reaction mixture was stirred at RT for 3 days
- customThe reaction mixture was evaporated to dryness
- customthe product was triturated
Sources & evidence
- ORD record
- ord-5cd2ebb4d2ad41ac9e5df482a6dd5243
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
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