Triethylamine → HCID 69652895, compound

HRID 1827471

Reaction equation

HRID 1827471 reaction equation
N1C=CC=CC=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.[CH3:28][N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([NH:36][NH2:37])=[O:35].C(N(CC)CC)C.CN(C(ON1N=N[C:55]2[CH:56]=[CH:57][CH:58]=[N:59][C:54]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:59]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1/[CH:7]=[CH:8]/[C:9]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][C:14]=2[NH:18][C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([NH:37][NH:36][C:34]([C:30]2[N:29]([CH3:28])[CH:33]=[CH:32][CH:31]=2)=[O:35])=[O:23])[NH:11][N:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27636101-methyl-1H-pyrrole-2-carbohydrazideHCID 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 69652895HCID 69652895, compoundYield 40.1%

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), 1-methyl-1H-pyrrole-2-carboxylic acid hydrazide (23.3 mg, 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 16.1 mg (40%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ 10.39 (1H, s), 10.00 (1H, s), 9.52 (1H, s), 8.67 (1H, d, J=2.4), 8.07 (4H, m), 7.77 (1H, d, J=5.2), 7.51 (4H, m), 7.32 (1H, s), 7.09 (1H, d, J=6.3), 6.98 (3H, m), 6.13 (1H, m), 3.87 (3H, s). ESIMS (M+H+):478.1.

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-12d9c302ed5c412ab8d0e528d1720e00
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Linked notes

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