Methylamine → HCID 44480346, compound

HRID 2067975Notes

Reaction equation

HRID 2067975 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@@H:9]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:20]=2[CH2:21]Br)=[O:15])[CH2:10][CH2:11][CH3:12])[CH:6]=[CH:7][CH:8]=1.C[NH2:33].C1COCC1>CN(C=O)C>[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@@H:9]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:20]=2[CH2:21][NH2:33])=[O:15])[CH2:10][CH2:11][CH3:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 58443390HCID 58443390, compound

Product 1

HCID 44480346HCID 44480346, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromomethyl-1-(4-chloro-phenyl)-1H-pyrazole-4-carboxylic acid [(S)-1-(3-trifluoromethyl-phenyl)-butyl]-amide (50 mg, 0.091 mmol) in DMF (2 mL) is treated with methylamine in THF (2.0 N solution, 49 μL, 0.091 mmol) and the resultant solution is heated in a microwave at 125° C. for 5 min. The crude reaction mixture is concentrated in vacuo and purified by preparative reverse phase HPLC (eluted with 10 to 90% CH3CN/H2O and 0.1% TFA as additive) to afford 5-aminomethyl-1-(4-chloro-phenyl)-1H-pyrazole-4-carboxylic acid [(S)-1-(3-trifluoromethyl-phenyl)-butyl]-amide (20 mg, 44%).

Workup

  1. customThe crude reaction mixture
  2. concentrationis concentrated in vacuo
  3. custompurified by preparative reverse phase HPLC (eluted with 10 to 90% CH3CN/H2O and 0.1% TFA as additive)

Sources & evidence

ORD record
ord-ff19966e993848b19f82e2464ac281be
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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