Sodium hydride → HCID 89962730, compound

HRID 337726

Reaction equation

HRID 337726 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19](F)=[CH:18][C:17]=1[F:24])(=[O:15])=[O:14])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[N:26]1([C@@H:31]2[CH2:36][CH2:35][CH2:34][CH2:33][C@@H:32]2[OH:37])[CH:30]=[CH:29][N:28]=[CH:27]1.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:25])[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([O:37][C@H:32]2[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]2[N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)=[CH:18][C:17]=1[F:24])(=[O:15])=[O:14])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 89964340HCID 89964340, compound

Product 1

HCID 89962730HCID 89962730, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 1a by using the tert-butyl[(5-chloro-2,4-difluorophenyl)sulfonyl](1,3-thiazol-4-yl)carbamic acid (WO 2010/079443; 390 mg, 0.949 mmol), (1S*,2R*)-2-(1H-imidazol-1-yl)cyclohexanol (Heterocycles, 31(3), 537-48, 1990; 160 mg, 0.963 mmol), sodium hydride (63%; 75.0 mg, 1.97 mmol) and DMF (4.0 mL), to yield the title compound (340 mg, 64%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-c3ffab929484460abc2af3bc136aff5e
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Linked notes

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