2-(Oxolan-3-yl)acetic acid → N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-(tetrahydrofuran-3-yl)acetamide

HRID 535514Notes

Reaction equation

HRID 535514 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].[O:20]1[CH2:24][CH2:23][CH:22]([CH2:25][C:26](O)=[O:27])[CH2:21]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:26](=[O:27])[CH2:25][CH:22]3[CH2:23][CH2:24][O:20][CH2:21]3)[N:11]=2)[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 42449052-(Oxolan-3-yl)acetic acidHCID 866735622-amino-4-(2-chloropyridin-4-yl)phthalazin-1(2H)-one

Product 1

HCID 71467635N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-(tetrahydrofuran-3-yl)acetamide

Procedure

The product from Example 29B and 2-(tetrahydrofuran-3-yl)acetic acid were processed using a method similar to that described in Example 10C to afford the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 8.60-8.60 (bs, 1H), 8.55-8.59 (m, 1H), 8.54-8.57 (m, 1H), 7.84-7.93 (m, 2H), 7.69-7.73 (m, 1H), 7.62 (s, 1H), 7.50-7.53 (m, 1H), 3.92-4.04 (m, 2H), 3.78-3.85 (m, 1H), 3.64-3.68 (m, 1H), 2.77-2.87 (m, 1H), 2.50-2.67 (m, 2H), 2.21-2.30 (m, 1H), 1.69-1.81 (m, 1H); MS (APCI+) M/Z 385 (M+H)+.

Sources & evidence

ORD record
ord-7d2e6d7921934b559f2c2b0026bdb89f
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

Loading…