Water → HCID 67348764, compound

HRID 1671289Notes

Reaction equation

HRID 1671289 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:9][N:10]2[C:13]2[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:6][CH:5]=1.Br[CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.O>CN(C)C=O>[CH:30]1([O:3][C:4]2[CH:12]=[C:11]3[C:7]([C:8]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[N:9][N:10]3[C:13]3[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=3)=[CH:6][CH:5]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 136003255HCID 136003255, compound

Product 1

HCID 67348764HCID 67348764, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (added with 40% mineral oil, 13.5 mg, manufactured by Kanto Chemical Co., Inc.) was added to a solution of ethyl 2-(6-hydroxy-3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylate (20 mg), which had been synthesized from the compound of Reference Example 20 according to the method of Example 3, in N,N-dimethylformamide (1 mL, manufactured by Kanto Chemical Co., Inc.) under ice cooling, and the mixture was stirred for 5 minutes at the same temperature. Subsequently, bromocyclopentane (269 mg, manufactured by Kanto Chemical Co., Inc.) was added, and the mixture was stirred overnight at room temperature. Water (10 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether (3×10 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1), to give 6.9 mg of the title compound. LC-MS: HPLC retention time 2.13 minutes, m/z 434 (M+H), condition C-1.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with diethyl ether (3×10 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was then evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-111361a7ff34494493994483041c9775
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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