4-Aminophenol → HCID 135839313, compound

HRID 2181562Notes

Reaction equation

HRID 2181562 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[N:2]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.CN(C(O[N:29]1N=N[C:31]2[CH:32]=[CH:33][CH:34]=N[C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:46]([CH3:49])[CH:47]=O>C(N(CC)CC)C>[NH:29]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:49]=2[N:46]=[C:47]1[C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[O:12])=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162279381H-indazole-6-carboxylic acid

Product 1

HCID 135839313HCID 135839313, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

To a solution of 3-1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid (208 mg, 0.7 mmol) in dry dimethylformamide (6 mL) was added 4-aminophenol (82 mg, 0.7 mmol) followed by HATU (312 mg, 0.8 mmol) and then triethylamine (20 drops) was added. The reaction was stirred overnight at room temperature. LC/MS showed desired product as major component. The solvent was removed by vacuum. The residue remaining was taken up in water and ethyl acetate. The layers were separated and the organic layer was concentrated under vacuum. The residue was dissolved in methanol (10 mL) and half of this solution was purified by HPLC using a gradient of 5% acetonitrile/water to 55% acetonitrile/water over 60 minutes with 0.1% trifluoroacetic acid in the water. The title compound was isolated as a solid (20 mg). 1H NMR (methanol-d4) 56.87 (2H, d, 8.8 Hz), 7.55 (2H, d, 8.7 Hz), 7.61 (2H, m), 7.87 (2H, br s), 8.00 (1H, d, 8.4 Hz), 8.35 (1H, s), 8.52 (1H, d, 8.6 Hz). MS (APCI pos) 370.1.

Sources & evidence

ORD record
ord-d6585ba34a624a469397457877ce3b2d
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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