2-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [3-(5-chloro-2-difluoromethoxy-phenyl)-1-piperidin-4-yl-1H-pyrazol-4-yl]-amide → 2-Amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [1-(3-amino-cyclobutyl)-3-(5-chloro-2-difluoromethoxy-phenyl)-1H-pyrazol-4-yl]-amide
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH:33]([F:35])[F:34])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[C:17]([NH2:25])=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH:26]3[CH2:31]C[NH:29][CH2:28][CH2:27]3)[N:9]=2)[CH:7]=1.C(OC(N[C@H]1C[C@H](OS(C2C=CC(C)=CC=2)(=O)=O)C1)=O)(C)(C)C>>[NH2:29][CH:28]1[CH2:31][CH:26]([N:10]2[CH:11]=[C:12]([NH:13][C:14]([C:16]3[C:17]([NH2:25])=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:32][CH:33]([F:35])[F:34])=[N:9]2)[CH2:27]1Participants
Reactant 2
Product 1
Procedure
The title compound was prepared in an analogous manner to 2-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [3-(5-chloro-2-difluoromethoxy-phenyl)-1-piperidin-4-yl-1H-pyrazol-4-yl]-amide using tert-butyl (3-((3-(5-chloro-2-(difluoromethoxy)phenyl)-1H-pyrazol-4-yl)carbamoyl)pyrazolo[1,5-a]pyrimidin-2-yl) carbamate and trans-toluene-4-sulfonic acid 3-tert-butoxycarbonylamino-cyclobutyl ester to afford the title compound as a white solid. LCMS (Method 5) [M+H]+=489.1, RT=2.87 min. 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 9.53 (s, 1H), 8.93 (dd, 1H, J=1.6, 6.8 Hz), 8.37-8.34 (m, 2H), 7.63-7.60 (m, 2H), 7.45 (d, 1H, J=7.2 Hz), 7.25 (t, 1H, J=72.6 Hz), 7.00 (dd, 1H, J=4.5, 6.5 Hz), 6.56 (s, 2H), 4.51-4.41 (m, 1H), 3.18-3.07 (m, 1H), 2.75-2.67 (m, 2H), 2.24-2.14 (m, 2H).
Sources & evidence
- ORD record
- ord-ee7791e123d34d938a41d97a918fada0
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346815B2
Reaction notes
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