Triethylamine → 1-(5-Pyrimidin-2-ylpyridin-2-yl)-4-{[(3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-yl]amino}cyclohexanol

HRID 2367044ノート

反応式

HRID 2367044 の反応式
[F:1][C:2]([F:24])([F:23])[C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([N:17]3[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18]3)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[OH:25][C:26]1([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[N:44]=[CH:43][CH:42]=[CH:41][N:40]=3)=[CH:35][N:34]=2)[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCl>[N:40]1[CH:41]=[CH:42][CH:43]=[N:44][C:39]=1[C:36]1[CH:37]=[CH:38][C:33]([C:26]2([OH:25])[CH2:31][CH2:30][CH:29]([NH:22][C@H:19]3[CH2:20][CH2:21][N:17]([C:15]([CH:12]4[CH2:11][CH2:10][N:9]([C:7]5[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:23])[F:24])[N:8]=5)[CH2:14][CH2:13]4)=[O:16])[CH2:18]3)[CH2:28][CH2:27]2)=[N:34][CH:35]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57803348(3S)-1-({1-[6-(Trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-amineHCID 578033584-Hydroxy-4-[5-(2-pyrimidinyl)-2-pyridyl]cyclohexanone

生成物 1

HCID 112733791-(5-Pyrimidin-2-ylpyridin-2-yl)-4-{[(3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-yl]amino}cyclohexanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-amine (40 mg, 0.1 mmol), 4-hydroxy-4-(5-pyrimidin-2-ylpyridin-2-yl)cyclohexanone (47 mg, 0.18 mmol), sodium triacetoxyborohydride (50 mg, 0.23 mmol), and triethylamine (35 mg, 0.35 mmol) in dichloromethane (10 mL) was stirred at room temperature overnight. The reaction mixture was passed through a silica gel pad. The filtrate was concentrated and purified by HPLC to give the cis- and trans-isomers. MS (M+H) 596.2 for both isomers.

後処理

  1. concentrationThe filtrate was concentrated
  2. custompurified by HPLC
  3. customto give the cis- and trans-isomers

出典と根拠

ORDレコード
ord-a0d7229f6303453dabe1e4dc685fd851
出典データセット
uspto-grants-2014_04
特許番号
US08697870B2

反応ノート

読み込み中…