6-Chloro-2-pyridinecarboxaldehyde → (S,E)-2-Cyano-3-(6-chloropyridin-2-yl)-N-(1-phenylbutyl)acrylamide

HRID 2406591Notes

Reaction equation

HRID 2406591 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](OCCN(CC)CC)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1.[Cl:33]C1N=C(C=O)C=CC=1.C(CC(N[C@H](C1C=CC=CC=1)CCC)=O)#N>>[C:31](/[C:9](=[CH:8]\[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:33])[N:7]=1)/[C:10]([NH:12][C@H:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16])=[O:11])#[N:32]

Participants

4

Reactant 3

HCID 107968486-Chloro-2-pyridinecarboxaldehydeHCID 56947930(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamideHCID 66822152(S)-2-cyano-N-(1-phenylbutyl)acetamide

Product 1

HCID 56947813(S,E)-2-Cyano-3-(6-chloropyridin-2-yl)-N-(1-phenylbutyl)acrylamide

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 33 except that 6-chloropicolinaldehyde was used instead of 6-bromopicolinaldehyde, and (S)-2-cyano-N-(1-phenylbutyl)acetamide 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 8:2 hexanes/ethyl acetate, to give 41 (105 mg, 95%) as a clear oil: MS (ES+) m/z340.1 (M+H)+.

Workup

  1. customThis produced the crude product which

Sources & evidence

ORD record
ord-8b8dd74304c64316929c402103b1993f
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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