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

HRID 968654

반응식

HRID 968654 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6f1b5f7ab23149a7abdb256e821d2de9
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304065B2

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