Benzylamine → HCID 9980952, compound

HRID 1827472Notes

Reaction equation

HRID 1827472 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21]([OH:23])=O)=[CH:15][CH:16]=2)[NH:11][N:10]=1.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:28]([NH:35][C:21](=[O:23])[C:20]1[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=1[NH:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9](/[CH:8]=[CH:7]/[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:10][NH:11]2)=[CH:16][CH:15]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 693529632-[3-(2-Pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzoic acid

Product 1

HCID 9980952HCID 9980952, compoundYield 120.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[3-(2-Pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzoic acid (50.0 mg, 0.084 mmol), benzylamine (18.2 μL, 0.17 mmol), triethylamine (58 μl, 0.42 mmol), dissolved in DMF (0.8 mL), was treated with HATU (48 mg, 0.13 mmol). The mixture was stirred overnight, then purified by reverse phase HPLC yielding 45.2 mg (76%) of the title compound as a TFA salt (1.5 H2O, 2.1 TFA, effective MW=711.98). 1H NMR (DMSO-d6): δ 9.86 (1H, s), 9.14 (1H, t, J=5.4), 8.73 (1H, d, J=4.8), 8.29 (4H, m), 7.56 (1H, d, J=7.0), 7.74 (2H, m), 7.89 (2H, m), 7.31 (5H, m), 7.16 (1H, d, J=7.8), 6.93 (1H, t, J=7.3), 4.46 (2H, d, J=6.1). ESIMS (M+H+): 446.5.

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-71953acbb417463580a29832dea2c099
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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