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

HRID 455922

Reaction equation

HRID 455922 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.[N:23]1[S:24][N:25]=[C:26]2[CH:31]=[C:30]([N:32]=[C:33]=[S:34])[CH:29]=[CH:28][C:27]=12.C(N(CC)CC)C>>[CH3:1][CH2:2][N:3]1[C:9]2[C:8](=[CH:13][N:12]=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:33]([NH:32][C:30]4[CH:29]=[CH:28][C:27]5[C:26](=[N:25][S:24][N:23]=5)[CH:31]=4)=[S:34])[CH2:16][CH2:15]3)[N:10]=2)[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1

Participants

4

Reactant 3

HCID 4831Pipemidic AcidHCID 8471TriethylamineHCID 27762922,1,3-Benzothiadiazol-5-yl isothiocyanate

Product 1

HCID 454841692-(4-{[(3-Benzothiadiazolphenyl)amino]carbonothioyl}-1-piperazinyl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic Acid

Procedure

Pipemidic acid (25 mg, 0.0824 mmol), 2,1,3-benzothiadiazol-5-yl isothiocyanate (15.8 mg, 0.0824 mmol) and triethylamine (23 μL, 0.165 mmol) were used. Purification on silica yielded compound 7 in Table 1, below (24 mg, 58%). 1H NMR (300 MHz, DMSO) δ 9.26 (s, 1H), 8.98 (s, 1H), 7.98-7.82 (m, 3H), 4.51-4.33 (m, 2H), 4.24-3.99 (m, 8H), 1.42-1.32 (m, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 7 in Table 1

Sources & evidence

ORD record
ord-1055adf2670945d680d887e10525002d
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Linked notes

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