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

HRID 469667Notes

Reaction equation

HRID 469667 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.[Br: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>>[Br: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 27288372-(3-Bromoadamantan-1-yl)acetic acidHCID 671617106-amino-4-phenylthieno[2,3-d]pyridazin-7(6H)-one

Product 1

HCID 671621712-(3-bromoadamantan-1-yl)-N-(7-oxo-4-phenylthieno[2,3-d]pyridazin-6(7H)-yl)acetamide

Procedure

The product from Example 29B and 2-(3-bromoadamantan-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 11.47 (s, 1H), 8.36 (d, J=5.2 Hz, 1H), 7.71-7.73 (m, 2H), 7.56-7.59 (m, 4H), 2.32-2.34 (m, 2H), 2.27-2.32 (m, 2H), 2.19-2.25 (m, 2H), 2.17 (s, 2H), 2.12-2.16 (m, 2H), 1.62-1.75 (m, 5H), 1.56-1.60 (m, 1H); MS (APCI+) M/Z 498 (M+H)+.

Sources & evidence

ORD record
ord-666b1f1b94774286938a3aed1acf60c7
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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