Ethyl Acetate → 1-(5-Pyrimidin-2-ylpyridin-2-yl)-4-{[(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-yl]amino}cyclohexanol

HRID 2367055Notes

Reaction equation

HRID 2367055 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][CH2:11][C:12]([N:14]2[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15]2)=[O:13])[CH:4]=1.[OH:22][C:23]1([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[N:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:32][N:31]=2)[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCOC(C)=O>CO.C(O)(C)C>[N:37]1[CH:38]=[CH:39][CH:40]=[N:41][C:36]=1[C:33]1[CH:34]=[CH:35][C:30]([C:23]2([OH:22])[CH2:28][CH2:27][CH:26]([NH:19][C@H:16]3[CH2:17][CH2:18][N:14]([C:12](=[O:13])[CH2:11][O:10][CH2:9][C:5]4[CH:4]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:8]=[CH:7][N:6]=4)[CH2:15]3)[CH2:25][CH2:24]2)=[N:31][CH:32]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 57803297(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-amineHCID 578033584-Hydroxy-4-[5-(2-pyrimidinyl)-2-pyridyl]cyclohexanone

Product 1

HCID 111571811-(5-Pyrimidin-2-ylpyridin-2-yl)-4-{[(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-yl]amino}cyclohexanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of (3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-amine (47 mg, 0.15 mmol) and 4-hydroxy-4-(5-pyrimidin-2-ylpyridin-2-yl)cyclohexanone (41 mg, 0.15 mmol) in methanol (2 mL) and isopropanol (2 mL) was added sodium triacetoxyborohydride (36 mg, 0.17 mmol). After being stirred at room temperature overnight, EtOAc was added. The solution was washed with NaHCO3 solution and water, dried (MgSO4) and concentrated. Purification by HPLC provided two isomers of the title compound. MS (M+H) 557.2 for both isomers.

Workup

  1. washThe solution was washed with NaHCO3 solution and water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-771d67ed8de1465fae32a0b6be363278
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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