Potassium Carbonate → 4'-Fluoro-biphenyl-4-carboxylic acid (6-piperidin-1-ylmethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-amide

HRID 968654

反応式

HRID 968654 の反応式
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:18][CH:17]=1)=[O:15])[CH2:7][CH2:6]2.Br[C:30](Br)([CH2:33][CH3:34])[CH2:31][CH3:32].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:1]1([CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH2:9][CH:8]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)=[CH:18][CH:17]=2)=[O:15])[CH2:7][CH2:6]3)[CH2:34][CH2:33][CH2:30][CH2:31][CH2:32]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 113947174'-Fluoro-biphenyl-4-carboxylic acid (6-aminomethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-amideHCID 135557303,3-Dibromopentane

生成物 1

HCID 112245284'-Fluoro-biphenyl-4-carboxylic acid (6-piperidin-1-ylmethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-amide収率 57%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4′-fluoro-biphenyl-4-carboxylic acid (6-aminomethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-amide, 4, (0.054 g, 0.14), dibromopentane (0.022 mL, 0.16 mmol) and K2CO3 (0.099 g, 0.72 mmol) in DMF (2 mL) is stirred at room temperature for 18 hours. The reaction solution is filtered and the filtrate concentrated in vacuo to leave a crude residue which is purified by reversed prep-HPLC using CH3CN—H2O (0.1% TFA) to afforded 36 mg (57% yield) of the desired product as a foaming solid. 1H NMR (300 MHz, CD3OD) δ 7.94 (d, J=8.4 Hz, 2H), 7.72 (m, 4H), 7.25 (t, J=9.6 Hz, 5H), 4.33 (m, 1H), 4.24 (s, 2H), 3.44-3.56 (m, 3H), 3.16-3.24 (br, 1H), 2.84-3.07 (m, 4H), 2.20-2.35 (br, 1H), 1.67-2.02 (m, 6H), 1.54 (m, H1); 13C NMR (75 MHz, CD3OD) δ 168.4, 164.8, 143.4, 137.4, 137.0, 130.9, 131.5, 130.0, 128.9, 128.8, 128.5, 127.9, 126.8, 115.8, 115.5, 60.5, 52.7, 46.6, 35.0, 28.9, 28.3, 22.9, 21.6; 19F NMR (282 MHz, CD3OD) δ 46.3; LRMS: 443.6 (M+H); HRMS: calcd for C29H32FN2O: 443.2499 (M+H), found: 443.2506.

後処理

  1. filtrationThe reaction solution is filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto leave a crude residue which
  4. customis purified by reversed

出典と根拠

ORDレコード
ord-6f1b5f7ab23149a7abdb256e821d2de9
出典データセット
uspto-grants-2007_12
特許番号
US07304065B2

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