beta-Phenylisovaleric acid → N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-3-methyl-3-phenylbutanamide

HRID 535504Notes

Reaction equation

HRID 535504 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19].[CH3:20][C:21]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:26])[CH2:22][C:23](O)=[O:24]>>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3](=[O:19])[N:2]([NH:1][C:23](=[O:24])[CH2:22][C:21]([CH3:20])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[N:11]=2)[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 13890beta-Phenylisovaleric acidHCID 866735622-amino-4-(2-chloropyridin-4-yl)phthalazin-1(2H)-one

Product 1

HCID 71467501N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-3-methyl-3-phenylbutanamide

Procedure

The product from Example 29B and 3-methyl-3-phenylbutanoic acid were processed using a method similar to that described in Example 10C to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.46 (s, 1H), 8.63 (dd, J=5.0, 0.7 Hz, 1H), 8.40-8.43 (m, 1H), 7.93-8.04 (m, 2H), 7.77-7.79 (m, 1H), 7.74 (dd, J=1.4, 0.7 Hz, 1H), 7.66 (dd, J=5.0, 1.5 Hz, 1H), 7.43-7.46 (m, 2H), 7.29-7.33 (m, 2H), 7.16-7.21 (m, 1H), 2.63 (s, 2H), 1.47 (s, 6H); MS (APCI+) M/Z 433 (M+H)+.

Sources & evidence

ORD record
ord-89fce78e4b474bed9badb27b30ef8eec
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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