HCID 19603776, compound → HCID 19603713, compound

HRID 1604674Notes

Reaction equation

HRID 1604674 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]3[O:26][C:25]([C:27]4[S:28][CH:29]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[N:31]=4)=[CH:24][C:23]=3[CH:36]=1)[N:13]=[C:12]2[C:37]([NH2:39])=[O:38])C1C=CC=CC=1>ClCCl>[C:32]([C:30]1[N:31]=[C:27]([C:25]2[O:26][C:22]3[CH:21]=[CH:20][C:19]([CH2:18][N:14]4[C:15]5[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=5)[C:12]([C:37]([NH2:39])=[O:38])=[N:13]4)=[CH:36][C:23]=3[CH:24]=2)[S:28][CH:29]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

3

Reactant 1

HCID 19603776HCID 19603776, compound

Product 1

HCID 19603713HCID 19603713, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Benzyloxy-1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-1H-indazole-3-carboxamide (0.122 g) was added to a solution (1 M) of borontribromide in dichloromethane (0.57 ml) under ice-cooling and then the mixture was stirred at room temperature for 1.5 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-hydroxy-1H-indazole-3-carboxamide (0.08 g).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7905e90813244e6ba2dcaa28ab9684f
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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