4-Pyridinemethanamine → N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-[(pyridin-4-ylmethyl)amino]ethyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 529786Notes

Reaction equation

HRID 529786 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[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][CH2:26][NH:27][CH2:28][CH2:29]SC)[N:9]=2)[CH:7]=1.Br[CH2:37][CH2:38][N:39]1[CH:43]=[C:42](NC(C2C=NN3C=CC=NC=23)=O)C(C2C=C(Cl)C=CC=2OC(F)F)=N1.N1C=CC(CN)=CC=1>>[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[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:25][CH2:26][NH:27][CH2:28][C:29]3[CH:42]=[CH:43][N:39]=[CH:38][CH:37]=3)[N:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 773174-PyridinemethanamineHCID 118522533N-[3-[5-chloro-2-(difluoromethoxy) phenyl]-1-(2-[[2-(methylsulfanyl)ethyl]amino]ethyl)-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 118522619N-[1-(2-bromoethyl)-3-[5-chloro-2-(difluoromethoxy) phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 118522532N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-[2-[(pyridin-4-ylmethyl)amino]ethyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Procedure

Using synthetic method analogous to that of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-(2-[[2-(methylsulfanyl)ethyl]amino]ethyl)-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide, the title compound was prepared from N-[1-(2-bromoethyl)-3-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide and pyridin-4-ylmethanamine. LCMS (Method 25) [M+H]+=539.1, RT=1.45 min. 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 9.74 (s, 1H), 9.34 (dd, 1H, J=1.6, 6.8 Hz), 8.68 (dd, 1H, J=1.6, 4.4 Hz), 8.45 (d, 2H, J=6.0 Hz), 8.38 (s, 1H), 7.64-7.59 (m, 2H), 7.44 (d, 1H, J=8.8 Hz), 7.32-7.28 (m, 3H), 7.07 (t, 1H, J=73.2 Hz), 4.26 (t, 2H, J=6.0 Hz), 3.76 (s, 2H), 2.93 (t, 2H, J=6.0 Hz).

Sources & evidence

ORD record
ord-2220ebfc9cb6458784961677e9fd959b
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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