Methanol → HCID 66841236, compound

HRID 1259526Notes

Reaction equation

HRID 1259526 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 hydro-chloride 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 hydro-chloride
  4. customare obtained in the form of a white powder

Sources & evidence

ORD record
ord-cd9aa9f66f774c33838f1cf6c25114f2
Source dataset
uspto-grants-2013_06
Patent number
US08466292B2

Reaction notes

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