Water → HCID 19603815, compound

HRID 1604703Notes

Reaction equation

HRID 1604703 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14]([OH:16])=[O:15].[C:17]([C:21]1[N:22]=[C:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][C:32]([CH2:35]Cl)=[CH:31][C:29]=3[CH:30]=2)[S:24][CH:25]=1)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:35][C:32]1[CH:33]=[CH:34][C:28]3[O:27][C:26]([C:23]4[S:24][CH:25]=[C:21]([C:17]([CH3:19])([CH3:18])[CH3:20])[N:22]=4)=[CH:30][C:29]=3[CH:31]=1)[N:9]=[C:8]2[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 103753065-methoxy-1H-indazole-3-carboxylic acidHCID 19603727HCID 19603727, compound

Product 1

HCID 19603815HCID 19603815, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

Sodium hydride (60% in mineral oil, 7.79 g) was added into a solution of 5-methoxy-1H-indazole-3-carboxylic acid (17.0 g) in N,N-dimethylformamide (400 ml) at room temperature under nitrogen atmosphere. After 30 minutes, 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (29.76 g) was added to the solution over 5 minutes. After being stirred continuously for 3 hours at 45° C., the reaction mixture was poured into water (2 l) and the reaction vessel was washed with water (200 ml). After combining the washing mixture to the aqueous mixture, the resulting mixture was made acidic with 10% hydrochloric acid aqueous solution (500 ml) and stirred vigorously for one hour. The precipitate was collected by filtration, washed with water and air-dried for one day. The crude product was washed with a mixture of isopropyl alcohol and isopropylethyl ether (7:3) and dried in vacuo to give 5-methoxy-1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indazole-3-carboxylic acid (36.5 g).

Workup

  1. washthe reaction vessel was washed with water (200 ml)
  2. stirringstirred vigorously for one hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customair-dried for one day
  6. washThe crude product was washed with a mixture of isopropyl alcohol and isopropylethyl ether (7:3)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-733af9862d9649bcaca1acf6c819ccc0
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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