Dimethylformamide → HCID 57861259, compound

HRID 1960006Notes

Reaction equation

HRID 1960006 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:28]([CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:29][CH3:30])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:20]([C:25]([OH:27])=O)[CH:19]=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.C(Cl)(=O)C(Cl)=O.[CH3:52][N:53](C=O)[CH3:54]>C(Cl)Cl>[CH3:52][N:53]([CH3:54])[C:25]([C:20]1[CH:19]=[C:18]2[C:23]([CH:24]=[C:15]([CH2:14][N:7]([CH2:6][C:5]3[CH:4]=[C:3]([C:2]([F:45])([F:44])[F:1])[CH:39]=[C:38]([C:40]([F:42])([F:41])[F:43])[CH:37]=3)[C:8]3[N:9]=[N:10][N:11]([CH3:13])[N:12]=3)[C:16]([N:28]([CH2:31][CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:29][CH3:30])=[N:17]2)=[CH:22][CH:21]=1)=[O:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57861273HCID 57861273, compound

Product 1

HCID 57861259HCID 57861259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-2-[N′-(cyclopentylmethyl)-N′-ethylamino]quinoline-7-carboxilic acid (30 mg, 0.047 mmol), oxalyl chloride (10 ul), and catalytic amount of DMF in CH2Cl2 (2 mL) is stirred at room temperature for 3 hours and concentrated in vacuo. The residue is dissolved with THF and treated with 2M dimethylamine in THF, and the resulting THF mixture is stirred at room temperature for 3 hours. The mixture is quenched by 1N HCl and extracted with EtOAc. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give 3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-2-[N′-(cyclopentylmethyl)-N′-ethylamino]quinoline-7-carboxylic acid dimethylamide.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved with THF
  3. additiontreated with 2M dimethylamine in THF
  4. stirringthe resulting THF mixture is stirred at room temperature for 3 hours
  5. customThe mixture is quenched by 1N HCl
  6. extractionextracted with EtOAc
  7. washThe organic layer is washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ebe650de27464b6bbe525b11a2c869e5
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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