2-Aminothiazole → HCID 59465996, compound

HRID 1876699Notes

Reaction equation

HRID 1876699 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)=[O:4].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1>N1C=CC=CC=1>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[NH:22][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH:6]2[CH2:7][CH2:8][CH2:9][N:5]2[C:3](=[O:4])[C:2]([F:21])([F:20])[F:1])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 59466191HCID 59466191, compound

Product 1

HCID 59465996HCID 59465996, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared using general procedure 37. Under an N2 atmosphere, a mixture of the 4-(1-(2,2,2-trifluoroacetyl)pyrrolidin-2-yl)benzene-1-sulfonyl chloride (1.1 g, 5.8 mmol), 2-aminothiazole (0.58 g, 5.8 mmol), and pyridine (4.0 mL) was stirred at RT for 19 h. The crude product was purified via silica gel chromatography using 3% MeOH in CH2Cl2. The resulting oil was taken up in a 2:1 mixture of CH2Cl2:Et2O (12 mL) and cooled to 0° C. for 20 minutes. The formed precipitate was filtered off and dried under vacuum to obtain N-(thiazol-2-yl)-4-(1-(2,2,2-trifluoroacetyl)pyrrolidin-2-yl)benzene-sulfonamide as a white solid (750 mg, 32%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=405.1; tR=2.68 min.

Workup

  1. customPrepared
  2. customThe crude product was purified via silica gel chromatography
  3. additionThe resulting oil was taken up in a 2:1 mixture of CH2Cl2
  4. temperatureEt2O (12 mL) and cooled to 0° C. for 20 minutes
  5. filtrationThe formed precipitate was filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-24636f3daf314897b7ce018927a73ee0
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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