Hydrochloride methanol → (S)-(4-Chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride

HRID 1051353Notes

Reaction equation

HRID 1051353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)[NH:9][S@@](C(C)(C)C)=O)=[CH:4][C:3]=1[F:22].Cl.CO>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)[NH2:9])=[CH:4][C:3]=1[F:22]

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86711993(R)-N-((S)-(4-chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86711994(S)-(4-Chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methanamine hydrochlorideYield 56%

Procedure

To a solution of 48 (2.9 g, 8.4 mmol) in MBTE (40 mL) was added 3N HCl/methanol (6.0 mL, 18 mmol). The mixture was stirred for 2 h at RT. The resulting solid was filtered and washed with MTBE to afford 650 mg (35%) of 50a. 1H NMR (500 MHz, CD3OD) δ 7.46-7.43 (m, 2H), 7.38 (s, 1H), 7.31 (dd, J=10.5, 2.0 Hz, 1H), 7.21 (dd, J=8.5, 1.5 Hz, 1H), 5.13 (s, 1H), 3.85 (s, 3H). LCMS (ESI) m/z: 240.0 [M+H]+.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with MTBE

Sources & evidence

ORD record
ord-db0f2b9f617a450dad78a270eb559625
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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