Pipemidic Acid → HCID 45484179, compound

HRID 455931Notes

Reaction equation

HRID 455931 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]([Cl:30])=[CH:26][C:25]=1[N:31]=[C:32]=[S:33]>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=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 1379152,5-Dichlorophenyl isothiocyanate

Product 1

HCID 45484179HCID 45484179, compound

Procedure

Pipemidic acid (51 mg, 0.168 mmol) and 2,5-dichlorophenyl isothiocyanate (20 μL, 0.140 mmol) were used. Purification on silica yielded compound 20 in Table 1, below (42.7 mg, 60%). 1H NMR (300 MHz, CDCl3) δ 9.39 (s, 1H), 9.06 (s, 1H), 7.57 (d, J=2.39 Hz, 1H), 7.42-7.36 (m, 1H), 7.20 (d, J=7.35 Hz, 1H), 4.55-4.39 (m, 2H), 4.31-4.02 (m, 8H), 1.52 (t, J=6.88 Hz, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 20 in Table 1

Sources & evidence

ORD record
ord-f2c7c14c901f4447b3bc42027a93d28a
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Reaction notes

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