Dimethylamine → 2-(3-((3-Amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)amino)-1H-pyrazol-1-yl)-N,N-dimethylacetamide

HRID 81075Notes

Reaction equation

HRID 81075 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[N:5]=[C:4]([NH:23][C:24]2[CH:28]=[CH:27][N:26]([CH2:29][C:30]([OH:32])=O)[N:25]=2)[CH:3]=1.[CH3:33][NH:34][CH3:35].CN(C(O[N:44]1[N:52]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NN>>[NH2:9][C:8]1[C:7]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:12][CH:11]=3)=[N:5][C:4]([NH:23][C:24]3[CH:28]=[CH:27][N:26]([CH2:29][C:30]([N:34]([CH3:35])[CH3:33])=[O:32])[N:25]=3)=[CH:3][C:2]=2[NH:52][N:44]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 9321HydrazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669271882-(3-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-ylamino)-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 696704832-(3-((3-Amino-4-(4-phenoxyphenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)amino)-1H-pyrazol-1-yl)-N,N-dimethylacetamide

Procedure

The acid from Step 2 of Example 248 and dimethylamine were coupled with HATU and subsequently reacted with hydrazine following conditions in Step 3 of Example 248 to give Example 249. 1H NMR (400 MHz, methanol-d4) δ ppm 7.91-7.97 (2H, m), 7.65 (1H, d, J=2.51 Hz), 7.47-7.54 (2H, m), 7.31 (1H, t, J=7.40 Hz), 7.18-7.24 (4H, m), 6.78 (1H, s), 6.05 (1H, d, J=2.26 Hz), 5.09 (2H, s), 3.03 (3H, s), 2.86 (3H, s); MS (ES+) m/z: 469.5 (M+H); LC retention time: 3.238 min (analytical HPLC

Workup

  1. customto give Example 249

Sources & evidence

ORD record
ord-16054371714e4b4c803d24d1b6f073d4
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

Loading…