Pyridine → HCID 178491359, compound

HRID 447924Notes

Reaction equation

HRID 447924 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[N:15]=1)=[NH:9].[C:27](Cl)(=[O:29])[CH3:28].N1C=CC=CC=1>C1COCC1>[C:27]([N:17]1[CH2:18][CH2:19][CH2:20][CH:16]1[C:14]1[N:15]=[C:11]([NH:10][C:8]([NH:7][CH2:6][C:5]2[C:4]([O:3][CH3:2])=[CH:24][CH:23]=[CH:22][C:21]=2[O:25][CH3:26])=[NH:9])[S:12][CH:13]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 178491363HCID 178491363, compound

Product 1

HCID 178491359HCID 178491359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 100 mg (0.25 mmol) N-(2,6-dimethoxybenzyl)-N′-(4-pyrrolidine-2-yl-1,3-thiazole-2-yl)guanidine hydrochloride, Example 147, 0.021 ml acetyl chloride and 0.04 ml pyridine in 10 ml THF were stirred for 1 hour at 5° C. and then 4 hours at room temperature. Chromatography of the crude product on RP-silica gel (Chromabond column, acetonitrile/water+0.1% glacial acetic acid; 0-100%) yielded 33 mg of the desired product; ESI-MS [M+H+]=404.15.

Workup

  1. custom4 hours
  2. customat room temperature

Sources & evidence

ORD record
ord-8a9d1ad6439a491eb54df1e74434a6e0
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Reaction notes

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