Pipemidic Acid → HCID 45484138, compound

HRID 455940Notes

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

Participants

Reactant 2

HCID 4831Pipemidic Acid

HCID 1510833-Iodophenylisothiocyanate

Product 1

HCID 45484138HCID 45484138, compound

Procedure

Pipemidic acid (40 mg, 0.133 mmol) and 3-iodophenyl isothiocyanate (29 mg, 0.111 mmol) were used. Purification on silica yielded compound 29 in Table 1, below (57 mg, 90%). 1H NMR (250 MHz, CDCl3) δ 9.33 (s, 1H), 8.73 (s, 1H), 7.66-7.64 (m, 1H), 7.54-7.51 (m, 1H), 7.40-7.24 (m, 1H), 7.12-7.06 (m, 1H), 4.48-4.31 (m, 2H), 4.27-3.93 (m, 8H), 1.34-1.17 (m, 3H) ppm.

Workup

customPurification on silica yielded compound 29 in Table 1

Sources & evidence

ORD record: ord-313685ca8c65454ea6ced39e5b6a2a69
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497371B2

Reaction notes

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