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 2103399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103399
[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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7dba6169513a4076a424377f576046b6
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576089B2

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