Water → 2-[(5-Phenyl-isoxazol-3-ylmethyl)-amino]-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

HRID 1178156Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[C:7]1([C:13]2[O:17][N:16]=[C:15]([CH2:18]OS(C)(=O)=O)[CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[NH2:25][CH2:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35](=[O:46])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]([F:45])([F:44])[F:43])[CH2:31][CH2:30]1)=[O:28].O>CN(C=O)C>[C:7]1([C:13]2[O:17][N:16]=[C:15]([CH2:18][NH:25][CH2:26][C:27]([N:29]3[CH2:30][CH2:31][N:32]([C:35](=[O:46])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]([F:45])([F:43])[F:44])[CH2:33][CH2:34]3)=[O:28])[CH:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

K2CO3 (201 mg, 1.46 mmol) was added to a stirred solution of methanesulfonic acid 5-phenyl-isoxazol-3-ylmethyl ester (200 mg, 0.73 mmol) and 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (257 mg, 0.73 mmol) in DMF (4 mL). The resulting mixture was heated at 40° C. for 1 hr. Cold water was then added and the resulting precipitate was isolated by filtration. The crude solid was purified by column chromatography using (silica gel of 60-120 mesh and 2% MeOH in CHCl3 as eluent) to afford 32 mg (9.2% yield) of 2-[(5-phenyl-isoxazol-3-ylmethyl)-amino]-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone. LCMS Purity: 96.53%. 1H NMR (DMSO-d6): δ 9.85 (s, 2H), 7.96-7.82 (m, 3H), 7.82-7.74 (t, 1H), 7.3 (d, 1H), 6.64-6.48 (d, 1H), 4.0-3.9 (d, 2H), 3.9-3.8 (m, 1H), 3.76-3.56 (m, 2H), 3.56-3.4 (m, 4H), 3.56-3.26 (bs, 1H), 3.2 (d, 2H), 2.49-2.29 (bs, 1H).

Workup

customthe resulting precipitate was isolated by filtration
customThe crude solid was purified by column chromatography

Sources & evidence

ORD record: ord-8cb2572de64c4f568e91a60b0c833918
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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