Acetic Acid → HCID 59153025, compound

HRID 1966863Notes

Reaction equation

HRID 1966863 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:20]=[N:21][C:22](Cl)=[C:23]([Br:25])[CH:24]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[H-].[Na+].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1.C(O)(=O)C>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:20]=[N:21][C:22]([O:37][C:34]4[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=4)=[C:23]([Br:25])[CH:24]=3)(=[O:17])=[O:18])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 44611236HCID 44611236, compound

Product 1

HCID 59153025HCID 59153025, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of [4-(5-Bromo-6-chloro-pyridine-3-sulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (50 mg, 0.10 mmol), sodium hydride (60% dispersed in mineral oil, 20 mg, 0.50 mmol) and 4-chlorophenol (0.4 mL, 3.79 mmol) in N,N-dimethylformamide (1.5 mL) was heated in a microwave oven at 100° C. for 15 minutes, then acidified with acetic acid to pH 5, filtered through a glass funnel and purified by preparative HPLC to afford {4-[5-bromo-6-(4-chloro-phenoxy)-pyridine-3-sulfonylamino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (30 mg, 52.6%) as a white powder. MS calcd for C22H22BrClN4O5S 548, obsd (ESI+) [(M+H)+]: 569.

Workup

  1. filtrationfiltered through a glass funnel
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6b80b076e61b4559a2875e7c62856446
Source dataset
uspto-grants-2013_04
Patent number
US08420675B2

Reaction notes

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