Acetic Acid → HCID 59153099, compound

HRID 1966870Notes

Reaction equation

HRID 1966870 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:17]([C:20]3[CH:25]=[CH:24][C:23](F)=[C:22]([Cl:27])[CH:21]=3)(=[O:19])=[O:18])[CH3:16])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[H-].[Na+].[Cl:31][C:32]1C=C[C:35](O)=[CH:34][CH:33]=1.[C:39]([OH:42])(=O)[CH3:40]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:42][C:39]4[CH:40]=[CH:35][CH:34]=[CH:33][C:32]=4[Cl:31])=[C:22]([Cl:27])[CH:21]=3)(=[O:19])=[O:18])[CH3:16])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 44611780HCID 44611780, compound

Product 1

HCID 59153099HCID 59153099, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

{(R)-4-[(3-Chloro-4-fluoro-benzenesulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (24 mg, 0.058 mmol), sodium hydride (60% dispersed in mineral oil, 11.6 mg) and 4-chlorophenol (0.52 mg, 0.40 mmol) were dissolved in N,N-dimethylformamide (2 mL). After being heated in a microwave oven at 100° C. for 15 minutes, the resulting mixture was acidified with acetic acid to pH 5, and filtered through a glass funnel. The precipitate was purified by preparative HPLC to afford ((R)-4-{[3-chloro-4-(2-chloro-phenoxy)-benzenesulfonyl]-methyl-amino}-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (24 mg, 77%) as a white powder. MS cald. for C24H25Cl2N3O5S 537, obsd. (ESI+) [(M+H)+]: 538.

Workup

  1. filtrationfiltered through a glass funnel
  2. customThe precipitate was purified by preparative HPLC

Sources & evidence

ORD record
ord-c6ea61563a5c464296d4f2c7c7ad5f9a
Source dataset
uspto-grants-2013_04
Patent number
US08420675B2

Reaction notes

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