1-Hydroxybenzotriazole → N-biphenyl-4-yl-3-[4-(2-tert-butyl-phenylamino)-piperidin-1-yl]-3-oxo-propionamide

HRID 1093677ノート

反応式

HRID 1093677 の反応式
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:13])[CH2:9][C:10]([OH:12])=O)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[C:53]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[NH:63][CH:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1)([CH3:56])([CH3:55])[CH3:54]>CN(C=O)C.O>[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:13])[CH2:9][C:10]([N:67]2[CH2:68][CH2:69][CH:64]([NH:63][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=3[C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:65][CH2:66]2)=[O:12])=[CH:5][CH:6]=1

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55049154N-biphenyl-4-yl-malonamic acidHCID 66591489(2-Tert-butyl-phenyl)-piperidin-4-yl-amine dihydrochloride

生成物 1

HCID 57874422N-biphenyl-4-yl-3-[4-(2-tert-butyl-phenylamino)-piperidin-1-yl]-3-oxo-propionamide収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of N-biphenyl-4-yl-malonamic acid (0.091 g, 0.00036 mole) in DMF (1 mL) was added DIPEA (0.211 g, 0.0016 mole), HOBt (0.048 g, 0.00036 mole) and EDCI.HCl (0.125 g, 0.00065 mole). After 2 minutes (2-tert-butyl-phenyl)-piperidin-4-yl-amine dihydrochloride (0.1 g, 0.00033 mole) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration. Purification by column chromatography using silica gel 60-120 mesh (1% methanol in chloroform) afforded 0.062 g (40%) of N-biphenyl-4-yl-3-[4-(2-tert-butyl-phenylamino)-piperidin-1-yl]-3-oxo-propionamide. LC-MS purity: 470.27 (M+1)+, 96.38%, 1H NMR (DMSO-d6): δ 7.8-7.6 (m, 6H), 7.5 (t, 2H), 7.3 (d, 1H), 7.1 (d, 1H), 7.0 (t, 1H), 6.8 (d, 1H), 6.6 (t, 1H), 4.3 (d, 1H), 3.9 (d, 2H), 3.7 (s, 1H), 3.6 (s, 2H), 3.2 (t, 1H), 2.9 (t, 1H), 2.0 (t, 2H), 1.5 (t, 1H), 1.4 (s, 9H).

後処理

  1. customthe resulting precipitate was isolated by filtration
  2. customPurification by column chromatography

出典と根拠

ORDレコード
ord-6138e41d16344bfd84ed0c0fd74c784e
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

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