6-Chloronicotinoyl Chloride → HCID 86661642, compound

HRID 404550Notes

Reaction equation

HRID 404550 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH:11]1([N:15]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1>>[ClH:1].[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:18]2[CH2:19][CH2:20][CH2:21][N:15]([CH:11]3[CH2:12][CH2:13][CH2:14]3)[CH2:16][CH2:17]2)=[O:7])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 574239531-Cyclobutyl-[1,4]diazepane

Product 1

HCID 86661642HCID 86661642, compound

Procedure

6-Chloronicotinic acid chloride (25.0 g, 137.8 mmol, 1 eq) was dissolved in 2-methyl-THF (328.0 g). A solution of 1-cyclobutyl-[1,4]diazepane (prepared as in Example 13 above, 24.1 g, 147.8 mmol, 1.05 eq) in 2-methyl-THF (164.0 g) was then added to the reaction mixture, while maintaining the temperature of the reaction mixture at less than 35° C. (about 45 min-1.5 hours). The resulting suspension was stirred at room temperature for 16 hours, then cooled to about 0-5° C. and maintained at 0° C. for 2 hours. The title compound was isolated by filtration, washed with 2-methyl-THF (2×45.0 g), then dried in vacuo at 60° C., to yield the title compound as a white solid.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at less than 35° C. (about 45 min-1.5 hours)
  2. temperaturecooled to about 0-5° C.
  3. temperaturemaintained at 0° C. for 2 hours

Sources & evidence

ORD record
ord-062fbdaff74e4f0a9c63e71f676fd3a8
Source dataset
uspto-grants-2014_06
Patent number
US08748596B2

Reaction notes

Loading…