Cyclopropanemethanamine → N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)-5-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 474339Notes

Reaction equation

HRID 474339 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=4)=[N:16][N:17]([CH3:19])[CH:18]=3)=[O:12])=[C:4]2[N:3]=1.[CH:27]1([CH2:30][NH2:31])[CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:26][C:22]1[CH:21]=[C:20]([C:15]2[C:14]([NH:13][C:11]([C:10]3[CH:9]=[N:8][N:5]4[CH:6]=[CH:7][C:2]([NH:31][CH2:30][CH:27]5[CH2:29][CH2:28]5)=[N:3][C:4]=34)=[O:12])=[CH:18][N:17]([CH3:19])[N:16]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 715122515-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 58063013N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)-5-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the above crude 5-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide, cyclopropylmethylamine (0.1 mL, 1.0 mmol), and N,N-diisopropylethylamine (0.20 mL, 1.1 mmol) in ethanol (5 mL) was heated at 120° C. by microwave irradiation. After 30 minutes, the reaction mixture was concentrated to dryness, and the resultant crude product was purified by reverse phase HPLC and lyophilized to give 95.7 mg (64%) of N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)-5-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=422.1; 1H NMR (500 MHz, DMSO) δ 9.62 (s, 1H), 8.58 (d, J=7.6, 1H), 8.20 (s, 1H), 8.14 (s, 2H), 7.75-7.59 (m, 2H), 7.46 (t, J=7.8, 1H), 7.42-7.34 (m, 1H), 6.41 (d, J=7.6, 1H), 3.90 (s, 3H), 2.62-2.54 (m, 2H), 0.76 (s, 1H), 0.38-0.24 (m, 2H), −0.14 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customthe resultant crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e0419cee473b49b58658c01b0ba1974c
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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