(E)-(2-(2-(2-(4-(1-(3-(6-Bromopyridin-2-yl)acrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl ester → N-(2-(2-(2-(4-(1-((E)-3-(6-Bromopyridin-2-yl)acrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

HRID 2406601Notes

Reaction equation

HRID 2406601 reaction equation
[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](\C#N)/[C:10]([NH:12][CH:13]([C:17]2[CH:47]=[CH:46][C:20]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][NH:30][C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][C@H:36]3[C@@H:43]4[C@@H:39]([NH:40][C:41](=[O:44])[NH:42]4)[CH2:38][S:37]3)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1.BrC1N=C(/C=C/C(NC(C2C=CC(OCCOCCOCCN(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=CC=2)CCC)=O)C=CC=1>>[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[CH:9]/[C:10]([NH:12][CH:13]([C:17]2[CH:18]=[CH:19][C:20]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][NH:30][C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][C@H:36]3[C@@H:43]4[C@@H:39]([NH:40][C:41](=[O:44])[NH:42]4)[CH2:38][S:37]3)=[CH:46][CH:47]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86762605(E)-(2-(2-(2-(4-(1-(3-(6-Bromopyridin-2-yl)acrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)imidodicarbonic acid, 1,3-bis-tert-butyl esterHCID 87168264N-(2-(2-(2-(4-(1-((E)-3-(6-Bromopyridin-2-yl)-2-cyanoacrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Product 1

HCID 87168521N-(2-(2-(2-(4-(1-((E)-3-(6-Bromopyridin-2-yl)acrylamido)butyl)phenoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 48 except that acrylamide 50 was used instead of cyanoacrylamide 47. This produced the crude product which was purified by flash silica gel column chromatography, eluting with 7:93 methanol/dichloromethane, to give 51 (50 mg, quantitative) 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-9f2778eee3994103bb0b59c26655ed81
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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