HCID 59128636, compound → HCID 59128623, compound

HRID 1991007Notes

Reaction equation

HRID 1991007 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][C:3]=1[C:11]1[C:22](=[O:23])[N:21]([CH3:24])[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=1>O=S(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]#[N:8])=[CH:4][C:3]=1[C:11]1[C:22](=[O:23])[N:21]([CH3:24])[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=1

Participants

3

Reactant 1

HCID 59128636HCID 59128636, compound

Product 1

HCID 59128623HCID 59128623, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Conditions

Temperature
75 °C

Procedure

4-Methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzamide (24 mg) was stirred in 3 g of SOCl2 for 100 hours at room temperature. Additional SOCl2 (4.5 g) was then added, and the reaction mixture was heated to 75° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was eluted with 5% MeOH in methylene chloride via preparative TLC plate to give 4-methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzonitrile: MS (M+H)=323.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was eluted with 5% MeOH in methylene chloride via preparative TLC plate

Sources & evidence

ORD record
ord-e2fa9a82fa7a4a68ae00586b70287e95
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

Loading…