2-Cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamide → (2-(2-(2-(4-(1-(2-Cyanoacetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

HRID 2406596Notes

Reaction equation

HRID 2406596 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(CC)CC)=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2].NC(C1C=CC(OCC[O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][N:43]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=CC=1)CCC>>[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][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][N:43]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])=[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 68041434(2-(2-(2-(4-(1-Aminobutyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

Product 1

HCID 68041433(2-(2-(2-(4-(1-(2-Cyanoacetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 29 except that (2-(2-(2-(4-(1-aminobutyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester (45) was used instead of 1-(4-(2-(diethylamino)ethoxy)phenyl)butan-1-amine (25). This produced the crude product which was purified by flash silica gel column chromatography, eluting with 3:2 hexanes/ethyl acetate, to give 46 (95 mg, 84%) as a clear oil: MS (ES+) m/z 564.3 (M+H)+.

Workup

  1. customThis produced the crude product which

Sources & evidence

ORD record
ord-765baba9861648eb9a06c8b2140a1492
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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