Thionyl Chloride → HCID 90114103, compound

HRID 2275783Notes

Reaction equation

HRID 2275783 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][CH:19]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:20]O)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.S(Cl)([Cl:34])=O>ClCCl>[ClH:34].[Cl:34][CH2:20][CH:19]([NH:18][C:16]([C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]3[C:2]([F:1])=[CH:30][CH:29]=[CH:28][C:27]=3[F:31])[C:7]2=[N:14][C:13]=1[CH3:15])=[O:17])[CH2:22][C:23]([F:26])([F:25])[F:24]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 90114193HCID 90114193, compound

Product 1

HCID 90114103HCID 90114103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.48 g of rac-8-[(2,6-difluorobenzyl)oxy]-2-methyl-N-(4,4,4-trifluoro-1-hydroxybutan-2-yl)-imidazo-[1,2-a]pyridine-3-carboxamide (Example 34A, 5.59 mmol) were initially charged in dichloromethane. At 0° C., 1.22 ml of thionyl chloride (16.77 mmol) were added dropwise, and the mixture was stirred at RT overnight. The reaction solution was concentrated and dried under high vacuum. This gave 2.78 g of the title compound (99.8% of theory).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-b2cc598b48424186b466958b56514d5b
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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