Triethylamine → 3-cyclopentyl-2-(3,4-dichloro-phenyl)-N-(4,5,6,7-tetrahydrobenzothiazol-2-yl)-propionamide

HRID 2304135

Reaction equation

HRID 2304135 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]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)CC)C.[NH2:53][C:54]1[S:55][C:56]2[CH2:62][CH2:61][CH2:60][CH2:59][C:57]=2[N:58]=1>CN(C)C=O.O.C(OCC)(=O)C>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:53][C:54]2[S:55][C:56]3[CH2:62][CH2:61][CH2:60][CH2:59][C:57]=3[N:58]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27627253-cyclopentyl-2-(3,4-dichlorophenyl)propanoic Acid

Product 1

HCID 120105423-cyclopentyl-2-(3,4-dichloro-phenyl)-N-(4,5,6,7-tetrahydrobenzothiazol-2-yl)-propionamideYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid (50 mg, 0.17 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (83 mg, 0.19 mmol), triethylamine (0.048 mL, 0.34 mmol), and 2-amino-4,5,6,7-tetrahydrobenzothiazole (40 mg, 0.26 mmol) in dry N,N-dimethylformamide (1 mL) was stirred at 25° C. for 14 h. The reaction mixture was then diluted with water and ethyl acetate, and the layers were separated. The organic layer was sequentially washed with a 1N aqueous hydrochloric acid solution, a saturated aqueous sodium chloride solution, and water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3,4-dichloro-phenyl)-N-(4,5,6,7-tetrahydrobenzothiazol-2-yl)-propionamide (56 mg, 79%) as a white solid: mp 170-171° C.; EI-HRMS m/e calcd for C21H24Cl2N2OS (M+) 422.0986, found 422.0982.

Workup

  1. customthe layers were separated
  2. washThe organic layer was sequentially washed with a 1N aqueous hydrochloric acid solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f90dc5a5c21f42acb7b38622853dacb1
Source dataset
uspto-grants-2002_08
Patent number
US06433188B1

Linked notes

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