Pipemidic Acid → 8-Ethyl-2-(4-((2-methoxyphenyl)carbamothioyl)piperazin-1-yl)-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid

HRID 455932

Reaction equation

HRID 455932 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.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[S:33]>>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32]([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:33]

Participants

3

Reactant 2

HCID 4831Pipemidic AcidHCID 5205992-Methoxyphenyl Isothiocyanate

Product 1

HCID 19202288-Ethyl-2-(4-((2-methoxyphenyl)carbamothioyl)piperazin-1-yl)-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid

Procedure

Pipemidic acid (53 mg, 0.175 mmol) and 2-methoxyphenyl isothiocyanate (20 μL, 0.145 mmol) were used. Purification on silica yielded compound 21 in Table 1, below (36 mg, 53%). 1H NMR (250 MHz, CDCl3) δ 9.33 (s, 1H), 8.68 (s, 1H), 7.84 (d, J=7.30 Hz, 1H), 7.54 (s, 1H), 7.20-7.04 (m, 1H), 7.03-6.85 (m, 2H), 4.44-3.73 (m, 13H), 1.49 (t, J=6.60 Hz, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 21 in Table 1

Sources & evidence

ORD record
ord-8877086194384d8383a0790690795a34
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Linked notes

Loading…