Diisopropylethylamine → 4-(4-Chloro-phenyl)-1-[1-(5,6-dimethyl-2-trifluoromethyl-pyrimidin-4-yl)-4-hydroxy-pyrrolidin-3-yl]-piperidin-4-ol

HRID 1920118Notes

Reaction equation

HRID 1920118 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:21])[CH2:14][CH2:13][N:12]([C@H:15]3[C@H:19]([OH:20])[CH2:18][NH:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[C:23]1[C:28]([CH3:29])=[C:27]([CH3:30])[N:26]=[C:25]([C:31]([F:34])([F:33])[F:32])[N:24]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:21])[CH2:14][CH2:13][N:12]([CH:15]3[CH:19]([OH:20])[CH2:18][N:17]([C:23]4[C:28]([CH3:29])=[C:27]([CH3:30])[N:26]=[C:25]([C:31]([F:33])([F:34])[F:32])[N:24]=4)[CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27365034-Chloro-5,6-dimethyl-2-(trifluoromethyl)pyrimidineHCID 66967966trans-4-(4-Chloro-phenyl)-1-(4-hydroxy-pyrrolidin-3-yl)-piperidin-4-ol hydrochloride

Product 1

HCID 586835724-(4-Chloro-phenyl)-1-[1-(5,6-dimethyl-2-trifluoromethyl-pyrimidin-4-yl)-4-hydroxy-pyrrolidin-3-yl]-piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared following general procedures described above from trans-4-(4-chloro-phenyl)-1-(4-hydroxy-pyrrolidin-3-yl)-piperidin-4-ol hydrochloride and 4-chloro-5,6-dimethyl-2-trifluoromethyl-pyrimidine in the presence of diisopropylethylamine and DMF. 1H-NMR (300 MHz, DMSO): δ 1.58 (2H, m), 1.89 (2H, m), 2.40 (3H, s), 2.60 (3H, m), 2.95 (2H, m), 3.32 (1H, m), 3.44 (1 H, m), 3.80 (2H, m), 4.32 (1H, m), 4.90 (1H, s), 5.20 (1H, d), 6.92 (1H, s), 7.42 (4H, dd). Retention Time (LC, method, AA standard): 1.75 min. MS (M+H+): 457

Workup

  1. custom1.75 min

Sources & evidence

ORD record
ord-90fd1c2a816c4d6a9d2e12a590e98fd7
Source dataset
uspto-grants-2012_05
Patent number
US08168788B2

Reaction notes

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