Triethylamine → HCID 71061873, compound

HRID 875475Notes

Reaction equation

HRID 875475 reaction equation
[NH2:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([C:11]([C:13]3[C:18]([Cl:19])=[CH:17][C:16]([Br:20])=[CH:15][C:14]=3[Cl:21])=[O:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.[CH2:22](N(CC)CC)[CH3:23].[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1.C([O:38][CH2:39][CH3:40])(=O)C>O1CCCC1>[Br:20][C:16]1[CH:15]=[C:14]([Cl:21])[C:13]([C:11]([N:10]2[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([N:1]([C:39]([CH:40]4[CH2:23][CH2:22]4)=[O:38])[C:32]([CH:29]4[CH2:31][CH2:30]4)=[O:33])[C:7]=3[CH:8]=[CH:9]2)=[O:12])=[C:18]([Cl:19])[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 77637Cyclopropanecarbonyl chlorideHCID 71061759HCID 71061759, compound

Product 1

HCID 71061873HCID 71061873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-amino-1H-pyrrolo[3,2-c]pyridin-1-yl)(4-bromo-2,6-dichlorophenyl)methanone (40 mg, 0.113 mmol) and triethylamine (0.23 mL, 0.206 mmol) in anhydrous tetrahydrofuran was treated dropwise with cyclopropane carbonyl chloride (0.01 mL, 0.11 mmol) under ice-cooled condition and stirred at room temperature for 1 hour. Ethyl acetate was added and washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulphate and concentrated to afford N-[1-(4-bromo-2,6-dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]-N-(cyclopropylcarbonyl)cyclopropanecarboxamide.

Workup

  1. temperaturecooled condition
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9dcd674c6f504365825db948062512cc
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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