Methylamine → 2-{4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}-N-methylacetamide

HRID 1778707Notes

Reaction equation

HRID 1778707 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[Cl:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([O:19][CH3:20])=[C:13]([Cl:21])[C:12]=1[C:22]1[N:27]=[CH:26][C:25]2[C:28]([C:31]3[CH:32]=[N:33][N:34]([CH2:36][C:37]([OH:39])=O)[CH:35]=3)=[N:29][NH:30][C:24]=2[CH:23]=1.CN.C1COCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:21][C:13]1[C:14]([O:19][CH3:20])=[CH:15][C:16]([O:17][CH3:18])=[C:11]([Cl:10])[C:12]=1[C:22]1[N:27]=[CH:26][C:25]2[C:28]([C:31]3[CH:32]=[N:33][N:34]([CH2:36][C:37]([NH:4][CH3:1])=[O:39])[CH:35]=3)=[N:29][NH:30][C:24]=2[CH:23]=1

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86722827{4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}acetic acid

Product 1

HCID 762852982-{4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (9.3 μL, 0.054 mmol) was added to a mixture of {4-[6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-3-yl]-1H-pyrazol-1-yl}acetic acid (8.0 mg, 0.018 mmol), 2.0 M methylamine in THF (9.8 μL, 0.020 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (8.7 mg, 0.020 mmol) in N,N-dimethylformamide (0.5 mL). The reaction mixture was stirred at r.t. for 3 h, and purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+=461.0/463.0.

Workup

  1. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-460fdad43e3b472d9484bd2104b9e211
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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