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

HRID 2406587Notes

Reaction equation

HRID 2406587 reaction equation
BrC1N=C(/C=C(\C#N)/C(NC(C2C=CC(OCCN(CC)CC)=CC=2)CCC)=O)C=CC=1.[F:33][C:34]1[N:39]=[C:38]([CH:40]=O)[CH:37]=[CH:36][CH:35]=1.[C:42]([CH2:44][C:45]([NH:47][CH:48]([C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]2[CH2:66][CH2:65][O:64][CH2:63][CH2:62]2)=[CH:54][CH:53]=1)[CH2:49][CH2:50][CH3:51])=[O:46])#[N:43]>>[C:42](/[C:44](=[CH:40]\[C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([F:33])[N:39]=1)/[C:45]([NH:47][CH:48]([C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]2[CH2:62][CH2:63][O:64][CH2:65][CH2:66]2)=[CH:54][CH:53]=1)[CH2:49][CH2:50][CH3:51])=[O:46])#[N:43]

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 668222832-Cyano-N-(1-(4-(2-morpholinoethoxy)phenyl)butyl)acetamide

Product 1

HCID 56947933(E)-2-Cyano-3-(6-fluoropyridin-2-yl)-N-(1-(4-(2-morpholinoethoxy)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-morpholinoethoxy)phenyl)butyl)acetamide (32) 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 37 (130 mg, 77%) 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-9d9bf9b7cb65450aa2e4c1e6d8f3d119
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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