Indazole-3-carboxylic acid → 1H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide

HRID 1807826Notes

Reaction equation

HRID 1807826 reaction equation
CCN(C(C)C)C(C)C.Cl.[CH2:11]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35](O)=[O:36])=[N:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([NH:23][C:35]([C:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:26][N:27]=2)=[O:36])=[CH:24][CH:25]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 78250Indazole-3-carboxylic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27238314-Benzyloxyaniline hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 93142921H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (9.3 mL, 53.4 mmol) was added to a solution of 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol), indazole-3-carboxylic acid (2.89 g, 17.8 mmol) and HBTU (7.1 g, 18.7 mmol) in DMF (60 mL), and the resulting solution was stirred at ambient temperature for 24 hours. The solution was heated to 70° C. for 4 hours, and then poured into a mixture of saturated aqueous sodium bicarbonate on ice. The product, an off white solid, 6.0 g, was collected by filtration, washed with water and used without further purification in the subsequent reaction. MS m/z 344 (MH+). 1H NMR (DMSO-d6) δ 5.11 (s, 2H), 7.02 (d, 2H), 7.26-7.48 (m, 7H), 7.67 (d, 1H), 7.75 (d, 2H), 7.81 (d, 1H), 8.24 (d, 1H) and 10.24 (s, 1H).

Workup

  1. temperatureThe solution was heated to 70° C. for 4 hours
  2. filtrationThe product, an off white solid, 6.0 g, was collected by filtration
  3. washwashed with water
  4. customused without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-dc8ff812db3a45b0bc8c22995e8aaab8
Source dataset
uspto-grants-2013_01
Patent number
US08357715B2

Reaction notes

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