6-Fluoropyridine-2-carboxaldehyde → (E)-2-Cyano-3-(6-fluoropyridin-2-yl)-N-(1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butyl)acrylamide

HRID 2406586Notes

Reaction equation

HRID 2406586 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][CH3:30])[CH2:27][CH3:28])=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1.[F:33]C1N=C(C=O)C=CC=1.C(CC(NC(C1C=CC(OCCN2CCCC2)=CC=1)CCC)=O)#N>>[C:31](/[C:9](=[CH:8]\[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:33])[N:7]=1)/[C:10]([NH:12][CH:13]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:29][CH2:30][CH2:28][CH2:27]2)=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16])=[O:11])#[N:32]

Participants

4

Reactant 3

HCID 106067416-Fluoropyridine-2-carboxaldehydeHCID 56947930(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamideHCID 668222012-Cyano-N-(1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butyl)acetamide

Product 1

HCID 56947934(E)-2-Cyano-3-(6-fluoropyridin-2-yl)-N-(1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butyl)acrylamide

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 33 except that 6-fluoropicolinaldehyde was used instead of 6-bromopicolinaldehyde, and 2-cyano-N-(1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)butyl)acetamide (31) 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 4:96 methanol/dichloromethane, to give 36 (65 mg, 35%) as a light yellow oil: MS (ES+) m/z 437.2 (M+H)+.

Workup

  1. customThis produced the crude product which

Sources & evidence

ORD record
ord-b2866fb3fcf84816845d76df2223d836
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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