Diisopropylethylamine → 7-Chloro-3-[4-(2-dimethylcarbamoyl-1,1-dimethyl-ethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1697072Notes

Reaction equation

HRID 1697072 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:26])[CH:8]=2)=[O:4].[NH2:33][C:34]([CH3:42])([CH3:41])[CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:23])[NH:33][C:34]([CH3:42])([CH3:41])[CH2:35][C:36](=[O:37])[N:38]([CH3:40])[CH3:39])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:26])[CH:8]=2)=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 187922133-amino-N,N,3-trimethylbutanamideHCID 251817183-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester

Product 1

HCID 251818547-Chloro-3-[4-(2-dimethylcarbamoyl-1,1-dimethyl-ethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-carboxy-benzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester (75 mg, 0.17 mmol), 3-amino-3,N,N-trimethyl-butyramide (24 mg, 0.17 mmol), BOP (150 mg, 0.34 mmol) and DIPEA (1 mL) in THF (15 mL) was stirred at RT overnight. The reaction mixture was partitioned between water and EtOAc, the organic layer separated, washed with water, dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by preparative TLC (EtOAc/hexane, 75:25) to yield 7-chloro-3-[4-(2-dimethylcarbamoyl-1,1-dimethyl-ethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (71 mg) as a light brown foam. MS=574 [M+H]+; MP=84.1-95.5° C.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. customthe organic layer separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by preparative TLC (EtOAc/hexane, 75:25)

Sources & evidence

ORD record
ord-67176f95793341b8ab7f66d9111cdb62
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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