Oxalyl chloride → HCID 86674848, compound

HRID 2405096Notes

Reaction equation

HRID 2405096 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)[CH3:3].C(Cl)(=O)C(Cl)=O.[CH2:19]([N:21]1[C:29]2[CH:28]=[C:27]([NH2:30])[N:26]=[CH:25][C:24]=2[C:23]([CH3:31])=[CH:22]1)[CH3:20]>C1(C)C=CC=CC=1.ClCCl>[CH2:19]([N:21]1[C:29]2[CH:28]=[C:27]([NH:30][C:8](=[O:10])[C:7]3[CH:6]=[CH:5][C:4]([C:2]([CH3:3])=[CH2:1])=[CH:12][CH:11]=3)[N:26]=[CH:25][C:24]=2[C:23]([CH3:31])=[CH:22]1)[CH3:20]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 2779194-(Prop-1-en-2-yl)benzoic acidHCID 86762595HCID 86762595, compound

Product 1

HCID 86674848HCID 86674848, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

In a 50 ml round bottom flask, 4-(prop-1-en-2-yl)benzoic acid (1.0 g, 6.3 mmol) was dissolved in 15 ml toluene and 2.0 M oxalyl dichloride (6.3 ml, 13 mmol) in dichloromethane was added slowly. Stirring continued for 3 hours, and then volatiles were evaporated from the reaction mixture. To the residue was added 5 ml toluene and the mixture was concentrated in vacuo to azeotropically remove residual water. The residue was then dissolved in DMA (10 ml) and 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridin-6-amine (1Q, 550 mg, 3.14 mmol) was added. Stirring continued at 50° C. overnight. The mixture was then poured into ice water. The precipitate was collected and dried to obtain the product N-(1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(prop-1-en-2-yl)benzamide (6B, 820 mg, 82%). This was used in the next step without further purification.

Workup

  1. customvolatiles were evaporated from the reaction mixture
  2. additionTo the residue was added 5 ml toluene
  3. concentrationthe mixture was concentrated in vacuo to azeotropically remove residual water
  4. dissolutionThe residue was then dissolved in DMA (10 ml)
  5. stirringStirring
  6. waitcontinued at 50° C. overnight
  7. customThe precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-fff6553218904b65b956477ce0376ee0
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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