Pipemidic Acid → HCID 1046489, compound

HRID 455928Notes

Reaction equation

HRID 455928 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][CH:27]=[CH:26][C:25]=1[N:30]=[C:31]=[S:32]>>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31]([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:32]

Participants

3

Reactant 2

HCID 4831Pipemidic AcidHCID 1231711-Chloro-2-isothiocyanatobenzene

Product 1

HCID 1046489HCID 1046489, compound

Procedure

Pipemidic acid (56 mg, 0.184 mmol) and 2-chlorophenylisothiocyanate (20 μL, 0.153 mmol) were used. Purification on silica yielded compound 17 in Table 1, below (72 mg, 99%). 1H NMR (300 MHz, CDCl3) δ 9.34 (s, 1H), 8.68 (s, 1H), 7.75 (d, J=8.10 Hz, 1H), 7.44 (d, J=8.00 Hz, 1H), 7.37-7.27 (m, 2H), 7.15 (t, J=7.67 Hz, 1H), 4.35 (q, J=7.15 Hz, 2H), 4.29-4.01 (m, 8H), 1.50 (t, J=7.20 Hz, 3H) ppm.

Workup

  1. customPurification on silica yielded compound 17 in Table 1

Sources & evidence

ORD record
ord-5f91a87b9bdd41dfbbfb842588c95c43
Source dataset
uspto-grants-2013_07
Patent number
US08497371B2

Reaction notes

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