2-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acid → N-[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]-2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetamide

HRID 469615Notes

Reaction equation

HRID 469615 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][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]1([CH3:32])[C@H:26]2[CH2:27][C@@H:22]1[CH2:23][CH2:24][C@H:25]2[CH2:28][C:29](O)=[O:30]>>[Cl:18][C:15]1[CH:16]=[CH:17][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:29](=[O:30])[CH2:28][C@@H:25]3[CH2:24][CH2:23][C@H:22]4[CH2:27][C@@H:26]3[C:21]4([CH3:20])[CH3:32])[N:11]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 671611162-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acidHCID 671613672-amino-4-(4-chlorophenyl)phthalazin-1(2H)-one

Product 1

HCID 67160999N-[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]-2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetamide

Procedure

The product of Example 86A and 2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetic acid (Eigenmann, G. W.; Arnold, R. T. JACS 1959, 81, 3440-2) were processed using a method similar to that described in Example 17C to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.38-11.39 (bs, 1H), 8.39-8.42 (m, 1H), 7.90-8.03 (m, 2H), 7.70-7.75 (m, 1H), 7.61-7.67 (m, 4H), 2.20-2.43 (m, 3H), 1.73-2.06 (m, 6H), 1.36-1.69 (m, 1H), 1.20 (s, 3H), 1.07 (s, 3H), 0.91 (d, J=9.5 Hz, 1H); MS (ESI+) m/z 436 (M+H)+.

Sources & evidence

ORD record
ord-6540e5dee2d246d5b08737238a41fd5d
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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