2-bromo-N-(4-methylpent-2-yn-4-yl)butyramide → 2-(3-cyano-6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide

HRID 2222303Notes

Reaction equation

HRID 2222303 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([OH:13])=[CH:8][CH:7]=2)#[N:2].Br[CH:15]([CH2:25][CH3:26])[C:16]([NH:18][C:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22])=[O:17]>>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:15]([CH2:25][CH3:26])[C:16]([NH:18][C:19]([CH3:24])([CH3:23])[C:20]#[C:21][CH3:22])=[O:17])=[CH:8][CH:7]=2)#[N:2]

Participants

3

Reactant 2

HCID 210784062-bromo-N-(4-methylpent-2-yn-4-yl)butyramideHCID 219231416-Hydroxy-3-quinolinecarbonitrile

Product 1

HCID 692546882-(3-cyano-6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide

Procedure

In a similar procedure to Example 6 Stage 2, 3-cyano-6-hydroxyquinoline was reacted with 2-bromo-N-(4-methylpent-2-yn-4-yl) butyramide to give 2-(3-cyano-6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide as a pale yellow solid, m.p. 116-118° C., 1H NMR (CDCl3) δ: 1.08(3H, t); 1.61(3H, s); 1.63(3H, s); 1.80(3H, s); 2.07-2.13(2H, m); 4.72(1H, t); 6.46(1H, s); 7.50 (1H, m); 7.57(1H, dd); 7.71(1H, d); 8.17(1H,d); 8.92(1H, d).

Sources & evidence

ORD record
ord-2dcc38aa240a4b02a4c3af4605544243
Source dataset
uspto-grants-2008_05
Patent number
US07371764B2

Reaction notes

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