Water → tert-Butyl ({4-[4-chloro-2-(2-formylpyridin-4-yl)phenoxy]-2,5-difluorophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate

HRID 46394Notes

Reaction equation

HRID 46394 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH:14]=[O:15])[CH:9]=2)[CH:7]=1.[S:17]1[CH:21]=[C:20]([N:22]([S:30]([C:33]2[CH:38]=[C:37]([F:39])[C:36](F)=[CH:35][C:34]=2[F:41])(=[O:32])=[O:31])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[N:19]=[CH:18]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][C:36]2[C:37]([F:39])=[CH:38][C:33]([S:30]([N:22]([C:20]3[N:19]=[CH:18][S:17][CH:21]=3)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:32])=[O:31])=[C:34]([F:41])[CH:35]=2)=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH:14]=[O:15])[CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 59436528tert-Butyl 1,3-thiazol-4-yl[(2,4,5-trifluorophenyl)sulfonyl]carbamateHCID 1360636234-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehyde

Product 1

HCID 59436611tert-Butyl ({4-[4-chloro-2-(2-formylpyridin-4-yl)phenoxy]-2,5-difluorophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehyde, (Preparation 880, 0.3 g, 0.0013 mol) and tert-butyl 1,3-thiazol-4-yl[(2,4,5-trifluorophenyl)sulfonyl]carbamate, (Preparation 297, 0.456 g, 0.0012 mol) were dissolved in dimethyl sulfoxide (5 mL) and potassium carbonate (0.355 g, 0.0026 mol) was added and reaction allowed to stir at room temperature for 2 hours. Water (10 mL) was added to the reaction, the resultant white precipitate was filtered off and dried in vacuo to give the title compound as a white solid (0.658 g).

Workup

  1. customreaction
  2. filtrationthe resultant white precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-389e3cfccdc0475582365aaf22782480
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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