Dimethylformamide → (R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl chloride

HRID 2038808Notes

Reaction equation

HRID 2038808 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][C@@:8]2([CH3:29])[N:12]3[C:13]([C:16]([OH:18])=O)=[CH:14][N:15]=[C:11]3[N:10]([C:19]3[CH:24]=[C:23]([Cl:25])[C:22]([F:26])=[C:21]([Cl:27])[CH:20]=3)[C:9]2=[O:28])=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)C([Cl:35])=O.CN(C=O)C>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@@:8]2([CH3:29])[N:12]3[C:13]([C:16]([Cl:35])=[O:18])=[CH:14][N:15]=[C:11]3[N:10]([C:19]3[CH:24]=[C:23]([Cl:25])[C:22]([F:26])=[C:21]([Cl:27])[CH:20]=3)[C:9]2=[O:28])=[CH:30][CH:31]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 58431190(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid

Product 1

HCID 86671823(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid (44 g, 95.8 mmol) was dissolved in CH2Cl2 (600 mL). To this solution was added oxalyl chloride (16.7 g) followed by DMF (0.3 mL). After 2 h, the volatiles were removed and the resultant residue was placed under high vacuum for 18 h to yield the title compound. The title compound was used without purification.

Workup

  1. customthe volatiles were removed
  2. waitthe resultant residue was placed under high vacuum for 18 h

Sources & evidence

ORD record
ord-2e9373cc1a4a498c96b878b619cdfbcd
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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