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

HRID 455937Notes

Reaction equation

HRID 455937 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][CH:27]=[CH:26][C:25]=1[N:30]=[C:31]=[S:32]>>[I:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[N:12]=[CH:13][C:8]3[C:6](=[O:7])[C:5]([C:20]([OH:22])=[O:21])=[CH:4][N:3]([CH2:2][CH3:1])[C:9]=3[N:10]=2)[CH2:15][CH2:16]1)=[S:32]

Participants

3

Reactant 2

HCID 4831Pipemidic AcidHCID 1453102-Iodophenyl isothiocyanate

Product 1

HCID 454841942-(4-{[(2-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) and 2-iodophenyl isothiocyanate (21.5 mg, 0.0824 mmol) were used. Purification on silica yielded compound 26 in Table 1, below (35 mg, 75%). 1H NMR (300 MHz, CDCl3) δ 9.36-9.30 (m, 1H), 8.69-8.65 (m, 1H), 7.89-7.82 (m, 1H), 7.62-7.55 (m, 1H), 7.41-7.32 (m, 1H), 7.00-6.92 (m, 1H), 4.40-4.01 (m, 10H), 1.53-1.44 (m, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 26 in Table 1

Sources & evidence

ORD record
ord-98cdfc6985d444968f02a9a51ef48f94
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Reaction notes

Loading…