Triethylamine → HCID 22992311, compound

HRID 1168458Notes

Reaction equation

HRID 1168458 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-2adde8394fc7441a86336ce7f8265252
Source dataset
uspto-grants-2003_09
Patent number
US06624175B2

Reaction notes

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