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

HRID 535518Notes

Reaction equation

HRID 535518 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][CH2:22][CH:21]1[CH2:25][C:26](O)=[O:27]>>[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:21]3[CH2:22][CH2:23][CH2:24][O:20]3)[N:11]=2)[CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 2287262-(Oxolan-2-yl)acetic acidHCID 866735622-amino-4-(2-chloropyridin-4-yl)phthalazin-1(2H)-one

Product 1

HCID 71467636N-[4-(2-chloropyridin-4-yl)-1-oxophthalazin-2(1H)-yl]-2-(tetrahydrofuran-2-yl)acetamide

Procedure

The product from Example 29B and 2-(tetrahydrofuran-2-yl)acetic acid were processed using a method similar to that described in Example 10C to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.46-11.62 (m, 1H), 8.63 (d, J=5.0 Hz, 1H), 8.40-8.43 (m, 1H), 7.93-8.06 (m, 2H), 7.75-7.79 (m, 2H), 7.69 (dd, J=5.0, 1.5 Hz, 1H), 4.16 (p, J=6.7 Hz, 1H), 3.79 (td, J=7.7, 6.1 Hz, 1H), 3.63 (td, J=7.8, 6.4 Hz, 1H), 2.57 (dd, J=14.2, 6.9 Hz, 1H), 2.44-2.52 (m, 1H), 1.99-2.07 (m, 1H), 1.78-1.95 (m, 2H), 1.57-1.66 (m, 1H); MS (APCI+) M/Z 385 (M+H)+.

Sources & evidence

ORD record
ord-c81b82eca1544c74a99a1f15e5a6bd53
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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