2-(1-Hydroxycyclohexyl)acetic acid → N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-(1-hydroxycyclohexyl)acetamide

HRID 535517Notes

Reaction equation

HRID 535517 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].[OH:20][C:21]1([CH2:27][C:28](O)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[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:28](=[O:29])[CH2:27][C:21]3([OH:20])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[N:11]=2)[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 2481532-(1-Hydroxycyclohexyl)acetic acidHCID 866735622-amino-4-(2-chloropyridin-4-yl)phthalazin-1(2H)-one

Product 1

HCID 86673563N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-(1-hydroxycyclohexyl)acetamide

Procedure

The product from Example 29B and 2-(1-hydroxycyclohexyl)acetic acid were processed using a method similar to that described in Example 10C to afford the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 9.29 (s, 1H), 8.58 (d, J=4.9 Hz, 1H), 8.52-8.57 (m, 1H), 7.82-7.93 (m, 2H), 7.70-7.72 (m, 1H), 7.62 (s, 1H), 7.50 (dd, J=5.0, 1.4 Hz, 1H), 2.62 (s, 2H), 1.79-1.90 (m, 3H), 1.65-1.74 (m, 2H), 1.52-1.65 (m, 5H), 1.28-1.38 (m, 1H)); MS (APCI+) M/Z 413 (M+H)+.

Sources & evidence

ORD record
ord-33a1fdb9752e44148371bf8909f2e581
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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