Sodium hydride → HCID 89963428, compound

HRID 337724Notes

Reaction equation

HRID 337724 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].[CH2:26]([N:28]1[C:32]([C@H:33]2[CH2:38][CH2:37][CH2:36]C[C@@H:34]2[OH:39])=[CH:31][CH:30]=[N:29]1)[CH3:27].[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:39][C@H:34]2[CH2:36][CH2:37][CH2:38][C@@H:33]2[C:32]2[N:28]([CH2:26][CH3:27])[N:29]=[CH:30][CH:31]=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 89962898(1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclohexanol

Product 1

HCID 89963428HCID 89963428, compoundYield 42.5%

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; 222 mg, 0.540 mmol), (1S*,2R*)-2-(1-ethyl-1H-pyrazol-5-yl)cyclohexanol (100 mg, 0.515 mmol) prepared in Example 12a, sodium hydride (63%; 39.2 mg, 1.03 mmol) and DMF (5.0 mL), to yield the title compound (125 mg, 41%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-11dccb570000438ab24b0200016e4013
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

Loading…