1-Adamantaneacetic acid → 2-(1-adamantyl)-N-(7-oxo-4-phenylthieno[2,3-d]pyridazin-6(7H)-yl)acetamide

HRID 469542Notes

Reaction equation

HRID 469542 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.[C:18]12([CH2:28][C:29](O)=[O:30])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2>>[C:18]12([CH2:28][C:29]([NH:1][N:2]3[C:7](=[O:8])[C:6]4[S:9][CH:10]=[CH:11][C:5]=4[C:4]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:3]3)=[O:30])[CH2:25][CH:24]3[CH2:23][CH:22]([CH2:21][CH:20]([CH2:26]3)[CH2:19]1)[CH2:27]2

Participants

3

Reactant 2

HCID 1232211-Adamantaneacetic acidHCID 671617106-amino-4-phenylthieno[2,3-d]pyridazin-7(6H)-one

Product 1

HCID 532374972-(1-adamantyl)-N-(7-oxo-4-phenylthieno[2,3-d]pyridazin-6(7H)-yl)acetamide

Procedure

The product from Example 29B and 2-(adamant-1-yl)acetic acid was processed using a method similar to that described in Example 17C to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.52-1.81 (m, 12H) 1.95 (s, 3H) 2.07 (s, 2H) 7.46-7.64 (m, 4H) 7.71 (dd, J=7.48, 1.98 Hz, 2H) 8.35 (d, J=5.49 Hz, 1H) 11.36 (s, 1H); MS (ESI) m/z 420 (M+H)+.

Sources & evidence

ORD record
ord-20d60516c66b492384560ba6d7079b6a
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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