Pipemidic Acid → HCID 1046490, compound

HRID 455935Notes

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

Participants

Reactant 2

HCID 4831Pipemidic Acid

HCID 752934-Methoxyphenyl isothiocyanate

Product 1

HCID 1046490HCID 1046490, compound

Procedure

Pipemidic acid (30 mg, 0.0989 mmol) and 4-methoxyphenyl isothiocyanate (13.7 μL, 0.0989 mmol) were used. Purification on silica yielded compound 24 in Table 1, below (37 mg, 80%). 1H NMR (300 MHz, CDCl3) δ 9.33 (s, 1H), 8.67 (s, 1H), 7.30 (s, 1H), 7.15 (d, J=8.76 Hz, 2H), 6.90 (d, J=8.82 Hz, 2H), 4.34 (q, J=7.10 Hz, 2H), 4.25-3.92 (m, 8H), 3.81 (s, 3H), 1.49 (t, J=7.12 Hz, 3H) ppm.

Workup

customPurification on silica yielded compound 24 in Table 1

Sources & evidence

ORD record: ord-2ebec1a6a08842ed929078a4bcb60987
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497371B2

Reaction notes

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