Methanol → HCID 66841236, compound

HRID 244064Notes

Reaction equation

HRID 244064 reaction equation
Cl.[Cl:2][C:3]1[C:4]([C:10]2[C:11]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([O:35][CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])[CH:29]=3)=[N:12][C:13]([C:16]([NH:18][C:19]3([C:25]([OH:27])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:17])=[CH:14][CH:15]=2)=[N:5][CH:6]=[C:7]([Cl:9])[CH:8]=1.S(Cl)(Cl)=O.[CH3:46]O>CCOCC>[ClH:2].[Cl:2][C:3]1[C:4]([C:10]2[C:11]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([O:35][CH2:36][CH2:37][CH2:38][N:39]([CH3:40])[CH3:41])[CH:29]=3)=[N:12][C:13]([C:16]([NH:18][C:19]3([C:25]([O:27][CH3:46])=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[O:17])=[CH:14][CH:15]=2)=[N:5][CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 66721057HCID 66721057, compound

Product 1

HCID 66841236HCID 66841236, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 300 mg (0.47 mmol) of 1-{[(3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridin-6′-yl)carbonyl]amino}cyclo-hexanecarboxylic acid hydrochloride in 10 mL of methanol and cooled to 0° C. is added 0.07 mL (0.93 mmol) of thionyl chloride. The reaction mixture is warmed to room temperature and stirred for 20 hours, and then concentrated under reduced pressure. The residue obtained is taken up in 20 mL of ether and solidified. After drying under reduced pressure, 268 mg of methyl 1-{[(3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridin-6′-yl)carbonyl]amino}cyclohexanecarboxylate hydrochloride are obtained in the form of a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. dry with materialAfter drying under reduced pressure, 268 mg of methyl 1-{[(3,5-dichloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-2,3′-bipyridin-6′-yl)carbonyl]amino}cyclohexanecarboxylate hydrochloride
  4. customare obtained in the form of a white powder

Sources & evidence

ORD record
ord-0501b2f64c114927b38ed21d387b5fdd
Source dataset
uspto-grants-2014_02
Patent number
US08653276B2

Reaction notes

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