Pipemidic Acid → HCID 1387411, compound

HRID 455934Notes

Reaction equation

HRID 455934 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.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[S:32])=[CH:26][CH:25]=1>>[F: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 152414-Fluorophenyl isothiocyanate

Product 1

HCID 1387411HCID 1387411, compound

Procedure

Pipemidic acid (35 mg, 0.1154 mmol) and 4-fluorophenyl isothiocyanate (17.7 mg, 0.1154 mmol) were used. Purification on silica yielded compound 23 in Table 1, below (30 mg, 57%). 1H NMR (300 MHz, CDCl3) δ 9.34 (s, 1H), 8.69 (s, 1H), 7.33 (s, 1H), 7.25-7.16 (m, 2H), 7.13-7.03 (m, 2H), 4.34 (q, J=7.00 Hz, 2H), 4.28-3.96 (m, 8H), 1.50 (t, J=7.36 Hz, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 23 in Table 1

Sources & evidence

ORD record
ord-b4aab6418f214b76ae5c1849d2b430a9
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Reaction notes

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