2-Aminothiazole → HCID 10361846, compound

HRID 854722Notes

Reaction equation

HRID 854722 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][O:15]2)[C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][O:15]2)[C:10]([NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21958994HCID 21958994, compound

Product 1

HCID 10361846HCID 10361846, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-propionic acid (204.5 mg, 0.70 mmol), 2-aminothiazole (71 mg, 0.70 mmol), and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (314 mg, 0.70 mmol) in N,N-dimethylformamide (3.55 mL) was treated with N,N-diisopropylethylamine (260 μL, 1.49 mmol). The mixture was stirred under nitrogen at 25° C. for 18 h. At this time, the reaction was diluted with water (50 mL). This solution was extracted with ethyl acetate (3×50 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(tetrahydro-furan-2-yl)-N-thiazol-2-yl-propionamide (232.2 mg, 88.4%) as a white solid: mp 69-71° C.; EI-HRMS m/e calcd for C16H16Cl2N2O2S (M+) 370.0309. found 370.0309.

Workup

  1. extractionThis solution was extracted with ethyl acetate (3×50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbf83e40bdbe4ffdb04bb83acef0aa9f
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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