Pipemidic Acid → HCID 2025521, compound

HRID 455939Notes

Reaction equation

HRID 455939 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.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[S:32])=[CH:26][CH:25]=1>>[Cl: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

3

Reactant 2

HCID 4831Pipemidic AcidHCID 164804-Chlorophenyl isothiocyanate

Product 1

HCID 2025521HCID 2025521, compound

Procedure

Pipemidic acid (58 mg, 0.191 mmol) and 4-chlorophenyl isothiocyanate (27 mg, 0.159 mmol) were used. Purification on silica yielded compound 28 in Table 1, below (50 mg, 67%). 1H NMR (300 MHz, CDCl3) δ 9.34 (s, 1H), 8.68 (s, 1H), 7.36-7.34 (m, 2H), 7.17 (d, J=8.70 Hz, 2H), 4.39-4.28 (m, 2H), 4.28-3.93 (m, 8H), 1.49 (t, J=6.68 Hz, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 28 in Table 1

Sources & evidence

ORD record
ord-98cd99ad3e9b47ac8be483e148b14bde
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Reaction notes

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