Lipoic acid → 5-[1,2]DITHIOLAN-3-YL-PENTANOIC Acid {6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZIN-3-YL}AMIDE

HRID 2056438Notes

Reaction equation

[CH2:1]1[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[S:4][S:3][CH2:2]1.[NH2:13][C:14]1[N:19]=[N:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])=[O:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1>>[F:37][C:34]([F:35])([F:36])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:26]([N:23]1[CH2:22][CH2:21][N:20]([C:17]2[N:18]=[N:19][C:14]([NH:13][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]3[CH2:1][CH2:2][S:3][S:4]3)=[CH:15][CH:16]=2)[CH2:25][CH2:24]1)=[O:27]

Participants

Reactant 2

HCID 6112Lipoic acid

HCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 865972105-[1,2]DITHIOLAN-3-YL-PENTANOIC Acid {6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZIN-3-YL}AMIDE

Procedure

Following the procedure of Example 2, making variations only as required to use lipoic acid in place of benzyloxyacetic acid to react with [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone, the title compound was obtained as a white solid (yield 8%). 1H NMR (300 MHz, CDCl3) δ 10.11, 8.37, 7.72, 7.61, 7.53, 7.35, 7.04, 4.08-3.84, 3.70-3.57, 3.56-3.46, 3.33-3.30, 3.17-3.02, 2.59, 2.39, 1.84, 1.78-1.56, 1.51-1.37. 13C NMR (300 MHz, CDCl3): 172.52, 167.57, 157.94, 150.00, 134.42, 132.38, 129.45, 127.79, 127.29, 127.14, 126.93, 126.88, 126.82, 121.92, 116.27, 56.34, 46.47, 45.65, 45.33, 41.25, 40.26, 38.49, 37.05, 34.74, 28.85, 25.14. MS (ES+) m/e 540.1 (M+1).

Sources & evidence

ORD record: ord-d45fbc7fdab6430c8b096c370601b073
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335658B2

Reaction notes

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