2-Aminothiazole → HCID 10223846, compound

HRID 2296933Notes

Reaction equation

HRID 2296933 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:17]([OH:19])=O)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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.[NH2:53][C:54]1[S:55][CH:56]=[CH:57][N:58]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.O>[CH:21]1([CH2:20][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:11][CH:12]=2)[C:17](=[O:19])[NH:53][C:54]2[S:55][CH:56]=[CH:57][N:58]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11163527HCID 11163527, compound

Product 1

HCID 10223846HCID 10223846, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-benzoylamino-phenyl)-3-cyclopentyl-propionic acid (20.2 mg, 0.06 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (39.8 mg, 0.09 mmol), and 2-aminothiazole (9.0 mg, 0.09 mmol) in methylene chloride (2 mL) at 25° C. was treated with N,N-diisopropylethylamine (0.25 mL, 0.18 mmol). The reaction mixture was stirred at 25° C. for 16 h. At this time, the mixture was poured into water (50 mL) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with a 1N aqueous hydrochloric acid solution (1×25 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded {N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-benzamide (95%) as a white solid: mp 285-290° C.; EI-HRMS m/e calcd for C24H25N3O2S (M+) 419.1667, found 419.1667.

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic extracts were washed with a 1N aqueous hydrochloric acid solution (1×25 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3f8d1ac16bf43e5b8f6293a950b19de
Source dataset
uspto-grants-2002_12
Patent number
US06489485B2

Reaction notes

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