Pyridine → HCID 86596236, compound

HRID 658088Notes

Reaction equation

HRID 658088 reaction equation
[Br:1][CH2:2][CH2:3][NH:4][C:5]([S:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([NH:12][C:13](=[O:17])[CH2:14][CH2:15][NH2:16])=[O:11])=[O:6].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[N+:22]1([CH2:2][CH2:3][NH:4][C:5]([S:7][C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[C:10]([NH:12][C:13](=[O:17])[CH2:14][CH2:15][NH2:16])=[O:11])=[O:6])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Br-:1]

Participants

3

Reactant 2

HCID 1049PyridineHCID 86596235HCID 86596235, compound

Product 1

HCID 86596236HCID 86596236, compoundYield 82%

Procedure

A solution of N-[2-(2-bromoethylcarbamylthio)benzoyl]-β-alaninamide (0.37 g, 1.0 mmol) in pyridine (5 ml) was stirred for 8 h under nitrogen. The pyridine was removed in vacuo, and the crude product was purified by column chromatography on silica using chloroform-methanol (7:3 v/v) as eluent. Yield: 82%. 1H NMR (DMSO-d6): 2.38 (t, 2H, CH2), 3.40 (q, 2H, CH2), 3.72 (q, 2H, CH2), 4.72 (t, 2H, CH2), 6.92 (brs, 1H, NH2), 7.36-7.58 (m, 5H, Ar—H, NH2), 8.26 (t, 2H, Py-H), 8.36 (t, 1H, NH), 8.52 (t, 1H, NH), 8.66 (t, 1H, Py-H), 9.12 (d, 2H, Py-H).

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe crude product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-9048980eab264b04865a177229c6bba0
Source dataset
uspto-grants-2011_12
Patent number
US08076372B2

Reaction notes

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