Triethylamine → HCID 22992311, compound

HRID 2227455Notes

Reaction equation

HRID 2227455 reaction equation
C1([C:7]2([C:17](O)=[O:18])[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)N2)C=CC=CC=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.[N:34]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.[NH2:54][C:55]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)([CH2:59][CH3:60])[C:56]([NH2:58])=[O:57]>C(Cl)Cl>[C:56]([C:55]([NH:54][C:17]([C:7]1[C:37]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:34]=[C:15]([C:14]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:16]=1)=[O:18])([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH2:59][CH3:60])(=[O:57])[NH2:58]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4986911HCID 4986911, compoundHCID 68836441HCID 68836441, compound

Product 1

HCID 22992311HCID 22992311, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-phenylquinolinecarboxylic acid (600 mg, 2.4 mmol) in 10 mL of CH2Cl2 containing 1 mL of triethylamine is added BOP (1.3 g, 2.9 mmol) followed by 2-amino-2-phenylbutanamide (500 mg, 2.8 mmol). The reaction mixture is stirred overnight at room temperature. The mixture is diluted with 20 mL of CH2Cl2, then washed with aqueous Na2CO3, aqueous citric acid and brine. After drying over Na2SO4, the solvent is evaporated to afford N-(1-Carbamoyl-1-phenylpropyl)-2-phenyl-4-quinolinecarboxamide (700 mg) as a pale yellow foam.

Workup

  1. washwashed with aqueous Na2CO3, aqueous citric acid and brine
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-2a2e33b3a7594a579e79e4e1ba41be84
Source dataset
uspto-grants-2002_07
Patent number
US06413982B1

Reaction notes

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