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

HRID 455920

Reaction equation

HRID 455920 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.[I:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[S:32])=[CH:26][CH:25]=1.C(N(CC)CC)C>>[I:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([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:32])=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 4831Pipemidic AcidHCID 8471TriethylamineHCID 749384-Iodophenylisothiocyanate

Product 1

HCID 454841932-(4-{[(4-Iodophenyl)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), 4-iodophenyl isothiocyanate (21.5 mg, 0.0824 mmol) and triethylamine (23 μL, 0.165 mmol) were used. Purification on silica yielded compound 3 in Table 1, below (36 mg, 77%). 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 8.66 (s, 1H), 7.66 (d, J=6.94 Hz, 1H), 7.37 (s, 1H), 7.27 (s, 1H), 7.00 (d, J=7.44 Hz, 1H), 4.33 (q, J=6.90 Hz, 2H), 4.21-3.99 (m, 8H), 1.49 (t, J=7.14 Hz, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 3 in Table 1

Sources & evidence

ORD record
ord-41ce2e4ee08f4ca38df9e84a7d56844d
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Linked notes

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