2-Aminothiazole → HCID 59465844, compound

HRID 1876682Notes

Reaction equation

HRID 1876682 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1>N1C=CC=CC=1>[S:25]1[CH:26]=[CH:27][N:28]=[C:24]1[NH:23][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([F:22])([F:21])[F:1])[CH2:6][CH2:7]2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 179734784-(1-(2,2,2-Trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 59465844HCID 59465844, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared using general procedure 15, method A. A solution of 4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzene-1-sulfonyl chloride (3 g, 8.43 mmol) and 2-aminothiazole (0.84 g, 8.43 mmol) in pyridine (2 ml) was stirred overnight at RT. The reaction was quenched with water, extracted with DCM, dried over Na2SO4, filtered and concentrated. Purification via silica gel chromatography using 0-5% methanol in DCM gave N-(thiazol-2-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide (1.78 g, 50% yield). LC/MS: (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z M+1 obs=420.3; tR=1.41 min.

Workup

  1. customPrepared
  2. customThe reaction was quenched with water
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-d92c250f22fc43ad877ac81732899b6e
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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