Pipemidic Acid → 2-(4-{[(3,5-Bis(trifluoromethyl)phenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

HRID 455929Notes

Reaction equation

[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1.[F:23][C:24]([F:39])([F:38])[C:25]1[CH:26]=[C:27]([N:35]=[C:36]=[S:37])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>>[F:23][C:24]([F:38])([F:39])[C:25]1[CH:26]=[C:27]([NH:35][C:36]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[N:12]=[CH:13][C:8]4[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4][N:3]([CH2:2][CH3:1])[C:9]=4[N:10]=3)[CH2:15][CH2:16]2)=[S:37])[CH:28]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:30]=1

Participants

Reactant 2

HCID 4831Pipemidic Acid

HCID 27333953,5-Bis(trifluoromethyl)phenyl isothiocyanate

Product 1

HCID 454841312-(4-{[(3,5-Bis(trifluoromethyl)phenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

Procedure

Pipemidic acid (40 mg, 0.132 mmol) and 3,5-bis(trifluoromethyl)phenyl isothiocyanate (20 μL, 0.110 mmol) were used. Purification on silica yielded compound 18 in Table 1, below (61 mg, 97%). 1H NMR (300 MHz, CDCl3) δ 9.30 (s, 1H), 8.68 (s, 1H), 8.62 (s, 1H), 7.94 (s, 2H), 7.62 (s, 1H), 4.42-4.05 (m, 10H), 1.51 (t, J=7.07 Hz, 3H) ppm.

Workup

customPurification on silica yielded compound 18 in Table 1

Sources & evidence

ORD record: ord-3a6821c70ecd49edbe469ff7a9a25aa1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497371B2

Reaction notes

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