1H-imidazole-2-carbaldehyde → (E)-2-Cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)-3-(1H-imidazol-2-yl)acrylamide

HRID 2406588Notes

Reaction equation

HRID 2406588 reaction equation
Br[C:2]1[N:7]=[C:6](/[CH:8]=[C:9](\[C:31]#[N:32])/[C:10]([NH:12][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]([CH2:29]C)[CH2:27]C)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])C=C[CH:3]=1.[NH:33]1C=CN=C1C=O.C(CC(NC(C1C=CC(OCCN(C)C)=CC=1)CCC)=O)#N>>[C:31](/[C:9](=[CH:8]\[C:6]1[NH:7][CH:2]=[CH:3][N:33]=1)/[C:10]([NH:12][CH:13]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:29])=[CH:21][CH:22]=1)[CH2:14][CH2:15][CH3:16])=[O:11])#[N:32]

Participants

4

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 56947930(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamideHCID 668219482-Cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)acetamide

Product 1

HCID 66822374(E)-2-Cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)-3-(1H-imidazol-2-yl)acrylamide

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 33 except that 1H-imidazole-2-carbaldehyde was used instead of 6-bromopicolinaldehyde, and 2-cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)acetamide (30) 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 8:92 methanol/dichloromethane, to give 38 (80 mg, 63%) as a light yellow oil: MS (ES+) m/z 453.2 (M+H)+.

Workup

  1. customThis produced the crude product which

Sources & evidence

ORD record
ord-cf145cade1c347efaa48c665435e1b03
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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