(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamide → (E)-(2-(2-(2-(4-(1-(3-(6-Bromopyridin-2-yl)-2-cyanoacrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

HRID 2406597Notes

Reaction equation

HRID 2406597 reaction equation
[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=C(\C#N)/C(NC(C2C=CC(OCCN(CC)CC)=CC=2)CCC)=O)[CH:5]=[CH:4][CH:3]=1.[C:33]([CH2:35][C:36]([NH:38][CH:39]([C:43]1[CH:72]=[CH:71][C:46]([O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][N:56]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[CH:45][CH:44]=1)[CH2:40][CH2:41][CH3:42])=[O:37])#[N:34]>>[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:35](\[C:33]#[N:34])/[C:36]([NH:38][CH:39]([C:43]2[CH:72]=[CH:71][C:46]([O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][N:56]([C:57]([O:59][C:60]([CH3:62])([CH3:63])[CH3:61])=[O:58])[C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])=[CH:45][CH:44]=2)[CH2:40][CH2:41][CH3:42])=[O:37])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 56947930(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamideHCID 68041433(2-(2-(2-(4-(1-(2-Cyanoacetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester

Product 1

HCID 88569330(E)-(2-(2-(2-(4-(1-(3-(6-Bromopyridin-2-yl)-2-cyanoacrylamido)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 33 except that (2-(2-(2-(4-(1-(2-cyanoacetamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester (46) was used instead of 2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamide (29). This produced the crude product which was purified by flash silica gel column chromatography, eluting with 7:3 hexanes/ethyl acetate, to give 47 (105 mg, 85%) as a clear oil: MS (ES+) m/z 731.2 (M+H)+.

Workup

  1. customThis produced the crude product which

Sources & evidence

ORD record
ord-edcaea63676b4c9489dcfe974885ce96
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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