Water → HCID 86720656, compound

HRID 875458Notes

Reaction equation

HRID 875458 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][CH:16]=[CH:15][C:14]=3[Cl:20])=[O:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[C:29]([O:31][CH3:32])=[O:30].O>O1CCCC1>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[C:11]([N:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:29](=[O:30])[O:31][CH3:32])[C:7]=2[CH:8]=[CH:9]1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 71061454HCID 71061454, compound

Product 1

HCID 86720656HCID 86720656, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-amino-1H-pyrrolo[3,2-c]pyridin-1-yl)(2,6-dichlorophenyl)methanone (50 mg, 0.16 mmol) and triethylamine (0.013 mL, 0.18 mmol) in anhydrous tetrahydrofuran was cooled to 0° C. and treated drop wise with methyl chloroformate (0.05 mL, 0.33 mL) and stirred at room temperature for 2 hours. The reaction mixture was poured onto cold water and the precipitated solid was filtered off, washed with hexane and dried to afford methyl [1-(2,6-dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]carbamate (35 mg, 60%).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. washwashed with hexane
  3. customdried

Sources & evidence

ORD record
ord-eb021d6ea71e4b58bfc98cb2c355da87
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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