2-Cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamide → 2-Cyano-N-(1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butyl)acetamide

HRID 2406581Notes

Reaction equation

HRID 2406581 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2].N1(CCOC2C=CC(C(N)CCC)=CC=2)CCCC1>>[C:1]([CH2:3][C:4]([NH:6][CH:7]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:23][CH2:24][CH2:22][CH2:21]2)=[CH:15][CH:16]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2]

Participants

3

Reactant 2

HCID 668220192-Cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamideHCID 668224831-(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)butan-1-amine

Product 1

HCID 668222012-Cyano-N-(1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butyl)acetamideYield 60%

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 29 except that 1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butan-1-amine (27) was used instead of 1-(4-(2-(diethylamino)ethoxy)phenyl)butan-1-amine (25). This produced crude product which was purified by flash silica gel column chromatography, eluting with 5:95 methanol/dichloromethane, to give 31 (140 mg, 60%) as a thick yellow oil: MS (ES+) m/z 330.2 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThis produced crude product which
  3. customwas purified by flash silica gel column chromatography
  4. washeluting with 5:95 methanol/dichloromethane

Sources & evidence

ORD record
ord-385e645a701a46dea0172df9018d5e5f
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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