Trifluoroacetic acid → 2-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate

HRID 710155ノート

反応式

HRID 710155 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[N:15][C:14]=3[CH:31]=2)=[CH:6][C:5]=1[F:32])(=[O:3])[NH2:2].[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>C(Cl)Cl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[F:32][C:5]1[CH:6]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[CH:31]=2)[CH:8]=[CH:9][C:4]=1[C:1]([NH2:2])=[O:3]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 71114210Tert-butyl 4-[5-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate

生成物 1

HCID 710895472-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Tert-butyl 4-[5-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate (140 mg, 0.32 mmol) dissolved in DCM (25 ml) and added trifluoroacetic acid (1 ml). This mixture stirred at rt for 3 h. After completion of the reaction, DCM removed on rotavapour and residue was co-distilled with ether to obtain 2-fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate (140 mg). 2-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate (140 mg, 0.31 mmol) was dissolved in DMF (5 ml) and added isovaleric acid (34.6 mg, 0.34 mmol), EDC.HCl (147 mg, 0.77 mmol), HOBt (50 mg, 0.37 mmol) and TEA (0.4 ml, 2.47 mmol). After completion of the reaction, water added to the reaction mixture to obtain solid. Solid was filtered and washed with ether to obtain the titled compound (20 mg) as a brown solid. M.P.: 186-190° C. MS (m/z): 424.1 [M+H]+.

後処理

  1. customremoved on rotavapour and residue

出典と根拠

ORDレコード
ord-8ed6bebd92224d49bee4aa5d513c5bf9
出典データセット
uspto-grants-2015_11
特許番号
US09181214B2

反応ノート

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