Ethanol → 3-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853046Notes

Reaction equation

HRID 1853046 reaction equation
[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[N:20]4[CH:21]=[CH:22][N:23]=[C:19]4[CH:18]=[C:17]([C:24]4[CH:29]=[CH:28][C:27](N5CCOCC5)=[CH:26][CH:25]=4)[N:16]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:36](O)[CH3:37]>>[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[N:20]4[CH:21]=[CH:22][N:23]=[C:19]4[CH:18]=[C:17]([C:24]4[CH:25]=[CH:26][C:27]([CH:37]5[CH2:36][CH2:15][N:20]([CH3:21])[CH2:19][CH2:18]5)=[CH:28][CH:29]=4)[N:16]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 702EthanolHCID 674582543-cyclopentyl-3-(4-(7-(4-morpholinophenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

Product 1

HCID 674556573-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrileYield 40%

Procedure

3-Cyclopentyl-3-(4-(7-(4-morpholinophenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (Example 113; 0.015 g, 0.032 mmol) was separated by chiral HPLC (Chiral Tech. OD-H, 2.2 cm×250 mm; 220 nm, 21 mL/min; 50% Ethanol: 50% Hexanes). Peak 1 was isolated to afford the single enantiomer 1 of 3-cyclopentyl-3-(4-(7-(4-(1-methylpiperidin-4-yl)phenyl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (6.0 mg, 40% yield). MS (apci) m/z=468.2 (M+H).

Workup

  1. customPeak 1 was isolated

Sources & evidence

ORD record
ord-cc284a20bf38451da60df48893f76f71
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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