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

HRID 469668Notes

Reaction equation

HRID 469668 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.[OH:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][C:21]([CH2:29][C:30](O)=[O:31])([CH2:22]3)[CH2:20]1)[CH2:26]2>>[OH:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][C:21]([CH2:29][C:30]([NH:1][N:2]4[C:7](=[O:8])[C:6]5[S:9][CH:10]=[CH:11][C:5]=5[C:4]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:3]4)=[O:31])([CH2:22]3)[CH2:20]1)[CH2:26]2

Participants

3

Reactant 2

HCID 4293072-(3-Hydroxyadamantan-1-yl)acetic acidHCID 671617106-amino-4-phenylthieno[2,3-d]pyridazin-7(6H)-one

Product 1

HCID 671608252-(3-hydroxyadamantan-1-yl)-N-(7-oxo-4-phenylthieno[2,3-d]pyridazin-6(7H)-yl)acetamide

Procedure

The product from Example 29B and 2-(3-hydroxyadamantan-1-yl)acetic acid 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 11.37 (s, 1H), 8.35 (d, J=5.2 Hz, 1H), 7.70-7.73 (m, 2H), 7.56-7.58 (m, 4H), 4.39 (s, 1H), 2.12 (s, 2H), 2.07-2.12 (m, 2H), 1.41-1.62 (m, 12H); MS (APCI+) M/Z 436 (M+H)+.

Sources & evidence

ORD record
ord-b1e4c304f3c648cf9a09a452a822ab56
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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