Oxalyl chloride → HCID 59729271, compound

HRID 600470Notes

Reaction equation

HRID 600470 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N:7]1([C:12]2[C:13]3[NH:20][CH:19]=C(C(O)=O)[C:14]=3[N:15]=[CH:16][N:17]=2)[CH:11]=[CH:10][CH:9]=[N:8]1>C(Cl)Cl.CN(C=O)C>[N:7]1([C:12]2[C:13]3[NH:20][CH:19]=[C:1]([C:2]([Cl:4])=[O:3])[C:14]=3[N:15]=[CH:16][N:17]=2)[CH:11]=[CH:10][CH:9]=[N:8]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 59729278HCID 59729278, compound

Product 1

HCID 59729271HCID 59729271, compoundYield 1,042.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.5 mL, 51 mmol) was added to a solution of diazaindole carboxylic acid 50 (1.08 g, 4.7 mmol) in CH2Cl2 (8 mL) and the reaction mixture was stirred 14 h. Catalytic DMF (3 drops) was added to the reaction mixture and after 3 h the reaction was quenched with MeOH. The crude reaction mixture was concentrated to dryness to yield 51 (1.21 g, 49 mmol, 96%) as a tan solid with was used without further purification. 1H NMR: (500 MHz, DMSO-d6) δ 12.45 (br s, 1H), 8.87 (s, 1H), 8.87 (d, J=2.6 Hz, 1H), 8.32 (d, J=3.3 Hz, 1H), 8.14 (d, J=1.5 Hz, 1H), 6.77 (dd, J=2.6, 1.5 Hz, 1H); Methyl ester (obtained by stirring 51 in MeOH): LC/MS: (ES+) m/z (M+H)+=244; HPLC Rt=0.95 min., column 0, conditions B.

Workup

  1. customwas quenched with MeOH
  2. customThe crude reaction mixture
  3. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-be9eda7b0b2f40349804e0bb41c6db86
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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