Ethanol → Isopropylaminium

HRID 1892771

反応式

HRID 1892771 の反応式
[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]

参加物

6

反応物 3

HCID 702EthanolHCID 6363IsopropylamineHCID 60152084HCID 60152084、化合物

生成物 2

HCID 3364502IsopropylaminiumHCID 60152084HCID 60152084、化合物

試薬・触媒・溶媒 1

HCID 280Carbon Dioxide溶媒

実験手順

(+\−)-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.

出典と根拠

ORDレコード
ord-2980624a347143d192d6ede07fa160ac
出典データセット
uspto-grants-2013_08
特許番号
US08507533B2

関連ノート

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