Triethylamine → 2-Phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid [1-(3-trifluoromethoxyphenyl)-ethyl]-amide

HRID 917300Notes

Reaction equation

[C:1]1([C:7]2[S:8][C:9]([C:16]([OH:18])=O)=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[F:52][C:53]([F:65])([F:64])[O:54][C:55]1[CH:56]=[C:57]([CH:61]([NH2:63])[CH3:62])[CH:58]=[CH:59][CH:60]=1.CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:52][C:53]([F:64])([F:65])[O:54][C:55]1[CH:56]=[C:57]([CH:61]([NH:63][C:16]([C:9]2[S:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:11][C:10]=2[C:12]([F:13])([F:14])[F:15])=[O:18])[CH3:62])[CH:58]=[CH:59][CH:60]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid (35 mg, 0.128 mmol) in DMF (1 mL) was added PyBOP (73 mg, 0.141 mmol) and DMAP (16 mg, 0.128 mmol). A solution of 1-(3-trifluoromethoxyphenyl)-ethylamine (27 mg, 0.128 mmol) in DMF (0.5 mL) was then added, followed by Et3N (36 μL, 0.256 mmol). This mixture was stirred at 25° C. for 18 h. The reaction mixture was applied directly to a preparatory HPLC column for purification (C18, 10-100% methanol/water/0.1% trifluoroacetic acid) which gave the amide as a white solid (24.9 mg, 42%).

Workup

customThe reaction mixture was applied directly to a preparatory HPLC column for purification (C18, 10-100% methanol/water/0.1% trifluoroacetic acid) which

Sources & evidence

ORD record: ord-9b62f3523ced4219bd5da00229e50548
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273866B2

Reaction notes

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