Triethylamine → 5-(4-Fluoro-phenyl)-2-methyl-thiazole-4-carboxylic Acid [2-(benzooxazol-2-ylamino)-ethyl]-amide

HRID 2376699Notes

Reaction equation

HRID 2376699 reaction equation
[NH2:1][CH2:2][CH2:3][N:4](C)[C:5]([C:7]1[N:8]=[C:9]([CH3:19])[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:6].C(N(CC)CC)C.Cl[C:29]1[O:30][C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=1>C1COCC1>[O:30]1[C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=[C:29]1[NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]=[C:9]([CH3:19])[S:10][C:11]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 687275705-(4-Fluoro-phenyl)-2-methyl-thiazole-4-carboxylic Acid (2-amino-ethyl)-methyl-amide

Product 1

HCID 101266535-(4-Fluoro-phenyl)-2-methyl-thiazole-4-carboxylic Acid [2-(benzooxazol-2-ylamino)-ethyl]-amideYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid (2-amino-ethyl)-methyl-amide, D5 (120 mg, 0.41 mmol) in THF (7 ml) was treated with triethylamine (0.057 ml) and 2-chlorobenzoxazole (0.047 ml, 0.41 mmol). The reaction mixture was stirred at room temperature, under argon for 16 h then the volatiles removed in vacuo. The residue was chromatographed (silica gel, 25% ethyl acetate-pentane) to afford the title compound as a white solid (97 mg, 58%).

Workup

  1. customthe volatiles removed in vacuo
  2. customThe residue was chromatographed (silica gel, 25% ethyl acetate-pentane)

Sources & evidence

ORD record
ord-7a1e79ec3a6c44308c3152c0bf6d7039
Source dataset
uspto-grants-2008_12
Patent number
US07468367B2

Reaction notes

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