Ethanol → Isopropylaminium

HRID 537553노트

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HRID 537553 반응식
[CH:1]1([CH:7]([NH:22][C:23]2[CH:24]=[N:25][C:26]([N:29]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[N:30]3)=[CH:27][CH:28]=2)[C:8]2[CH:21]=[CH:20][C:11]([C:12]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[CH:41]([NH2:44])([CH3:43])[CH3:42]>C(=O)=O>[CH:1]1([CH:7]([NH:22][C:23]2[CH:24]=[N:25][C:26]([N:29]3[CH:33]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:31]=[N:30]3)=[CH:27][CH:28]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:13])=[CH:20][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:41]([NH3+:44])([CH3:43])[CH3:42]

참가 물질

6

반응물 3

HCID 702EthanolHCID 6363IsopropylamineHCID 60152084HCID 60152084, 화합물

생성물 2

HCID 3364502IsopropylaminiumHCID 60152084HCID 60152084, 화합물

시약·촉매·용매 1

HCID 280Carbon Dioxide용매

실험 절차

(+\)-3-(4-(cyclohexyl(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine-3-ylamino)methyl)benzamido)propanoic acid (Example 101) was resolved by SFC (Column: Chiralpak AD-H 25×4.6 mm; mobile phase: 25% ethanol in CO2; modifier: 0.2% isopropylamine; flow rate: 2.5 mL/min) to provide 3-(4-(cyclohexyl(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine-3-ylamino)methyl)benzamido)propanoic acid, Isomer 1 (retention time: 6.93 min) and 3-(4-(cyclohexyl(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine-3-ylamino)methyl)benzamido)propanoic acid, Isomer 2 (retention time: 9.58 min) as their isopropylammonium salts. The salts were dissolved in water and the pH adjusted to 3.5 by addition of 1N aqueous HCl. The mixtures were extracted with dichloromethane. The organic layers were dried over MgSO4 and concentrated to provide 3-(4-(cyclohexyl(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine-3-ylamino)methyl)benzamido)propanoic acid, Isomer 1 and 3-(4-(cyclohexyl(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine-3-ylamino)methyl)benzamido)propanoic acid, Isomer 2. Spectral data for Isomer 1: 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 7.77 (s, 1H), 7.65-7.72 (m, 3H), 7.60 (d, J=8.8 Hz), 7.32 (d, J=8.2 Hz, 2H), 6.82-6.88 (m, 1H), 6.71-6.78 (m, 1H), 4.15 (d, J=6.2 Hz, 1H), 3.65-3.73 (m, 2H), 2.63-2.73 (m, 2H), 1.83-1.93 (m, 1H), 1.59-1.82 (m, 4H), 1.46-1.56 (m, 1H), 0.94-1.28 (m, 6H). MS (M+H)=516.2.

출처 및 근거

ORD 기록
ord-e4cec7ae28d84436a47ca59ed6ab53e0
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859591B2

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