2-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acid → 2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-N-(7-oxo-4-phenylthieno[2,3-d]pyridazin-6(7H)-yl)acetamide

HRID 469543Notes

Reaction equation

HRID 469543 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[S:9][CH:10]=[CH:11][C:5]=2[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3]1.[CH3:18][C:19]1([CH3:30])[C@H:24]2[CH2:25][C@@H:20]1[CH2:21][CH2:22][C@H:23]2[CH2:26][C:27](O)=[O:28]>>[CH3:18][C:19]1([CH3:30])[C@H:24]2[CH2:25][C@@H:20]1[CH2:21][CH2:22][C@H:23]2[CH2:26][C:27]([NH:1][N:2]1[C:7](=[O:8])[C:6]2[S:9][CH:10]=[CH:11][C:5]=2[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3]1)=[O:28]

Participants

3

Reactant 2

HCID 671611162-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acidHCID 671617106-amino-4-phenylthieno[2,3-d]pyridazin-7(6H)-one

Product 1

HCID 532377392-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-N-(7-oxo-4-phenylthieno[2,3-d]pyridazin-6(7H)-yl)acetamide

Procedure

The product from Example 29B and 2-[(1S,2S,55)-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 (500 MHz, DMSO-d6) δ ppm 0.91 (d, J=9.76 Hz, 1H) 1.08 (s, 3H) 1.20 (s, 3H) 1.39-1.66 (m, 1H) 1.76-2.05 (m, 5H) 2.20-2.46 (m, 4H) 7.45-7.65 (m, 4H) 7.71 (dd, J=7.63, 1.83 Hz, 2H) 8.35 (d, J=5.19 Hz, 1H) 11.46 (s, 1H); MS (ESI) m/z 408 (M+H)+.

Sources & evidence

ORD record
ord-5149ce869e4a45408f7f76be8eca545f
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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