Isobutyric Acid → 2-Fluoro-4-[2-(1-isobutyrylpiperidin-4-yl)benzo[d]oxazol-5-yl]benzamide

HRID 710161ノート

反応式

HRID 710161 の反応式
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]3[O:25][C:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[N:23][C:22]=3[CH:32]=2)[CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12].[C:33](O)(=[O:37])[CH:34]([CH3:36])[CH3:35].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[F:8][C:9]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]3[O:25][C:24]([CH:26]4[CH2:31][CH2:30][N:29]([C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[CH2:28][CH2:27]4)=[N:23][C:22]=3[CH:32]=2)[CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12]

参加物

7

反応物 4

HCID 6590Isobutyric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 710895472-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate

生成物 1

HCID 711144652-Fluoro-4-[2-(1-isobutyrylpiperidin-4-yl)benzo[d]oxazol-5-yl]benzamide収率 69.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Tert-butyl 4-[5-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate (190 mg, 0.32 mmol) dissolved in DCM (40 ml) and added trifluoroacetic acid (1.5 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 (190 mg). 2-Fluoro-4-(2-(piperidin-4-yl)-benzo[d]oxazol-5-yl)-benzamide 2,2,2-trifluoroacetate (190 mg, 0.42 mmol) was dissolved in DMF (7 ml) and added isobutyric acid (47 mg, 0.46 mmol), EDC.HCl (200 mg, 1.04 mmol), HOBt (70 mg, 0.5 mmol) and TEA (0.7 ml, 3.3 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 (120 mg) as a brown solid. M.P.: 193-196° C. MS (m/z): 410.2 [M+H]+.

後処理

  1. additionadded to the reaction mixture
  2. customto obtain solid
  3. filtrationSolid was filtered
  4. washwashed with ether

出典と根拠

ORDレコード
ord-87b48dfb3e94458f8fd7a150b4fc8524
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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