Morpholine → HCID 69517949, compound

HRID 1180017Notes

Reaction equation

HRID 1180017 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]([CH3:32])([CH2:11][C:12](=[O:31])[NH:13][C:14]1[CH:15]=[N:16][C:17]([O:20][C:21](=[O:30])[N:22]([CH3:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:19]=1)[CH2:7][C:8]([OH:10])=O.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>ClCCl>[CH3:5][C:6]([CH3:32])([CH2:7][C:8]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:10])[CH2:11][C:12]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:30])[N:22]([CH3:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:16][CH:15]=1)=[O:31]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 22047706HCID 22047706, compound

Product 1

HCID 69517949HCID 69517949, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionylchloride (237 microL, 3.27 mmol) was added to a stirred solution of 3,3-dimethyl-4-[6-(methyl-phenyl-carbamoyloxy)-pyridin-3-ylcarbamoyl]-butyric acid (0.63 g, 1.63 mmol) in dichloromethane (10 mL). After stirring for 10 minutes the solution was divided into 4 equal portions of acid chloride. To one portion was added morpholine (0.5 mL) and after stirring for 2 hours at room temperature the crude product was purified by flash column chromatography (SiO2), yielding the title compound (117 mg, 63% yield).

Workup

  1. customwas purified by flash column chromatography (SiO2)

Sources & evidence

ORD record
ord-bd5b994f0f40491e8aba8d90fca2b00a
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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