2-Aminothiazole → HCID 10159539, compound

HRID 1935198Notes

Reaction equation

HRID 1935198 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:60][C:61]1[S:62][CH:63]=[CH:64][N:65]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)[C:8]([NH:60][C:61]2[S:62][CH:63]=[CH:64][N:65]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22467935HCID 22467935, compound

Product 1

HCID 10159539HCID 10159539, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid (100 mg, 0.29 mmol) in dry N,N-dimethylformamide (2 ml,) was treated with O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (110 mg, 0.29 mmol), N,N-diisopropylethylamine (61 μL, 0.35 mmol), and 2-aminothiazole (45 mg, 0.44 mmol). The reaction mixture was stirred at 25° C. under nitrogen for 15 h. The reaction mixture was poured into a mixture of water and ethyl acetate (1:1), and the layers were separated. The organic layer was washed with a 1N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 2/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-N-thiazol-2-yl-propionamide (92 mg, 74%) as a white foam: mp 202-204° C.; FAB-HRMS m/e calcd for C27H26N2OS (M+H)+ 427.1844, found 427.1837.

Workup

  1. customthe layers were separated
  2. washThe organic layer was 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-ecc02ad6554c40bea83a96602f1d44c6
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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