Triethylamine → HCID 67793716, compound

HRID 1590251Notes

Reaction equation

HRID 1590251 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:20][CH:21]1[C:25](=[O:26])[N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[CH2:23][CH:22]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(N(CC)CC)C>C(Cl)Cl>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:24]1[C:25](=[O:26])[C@H:21]([NH:20][C:11]([C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[O:13])[C@H:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80971Quinoline-3-carboxylic acidHCID 19023603HCID 19023603, compound

Product 1

HCID 67793716HCID 67793716, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-quinolinecarboxylic acid (118 mg, 0.68 mmol) in CH2Cl2 (3 ml) was added oxalyl chloride (0.12 ml, 1.36 mmol) and the solution was stirred for 2.5 h. Removal of the solvent in vacuo gave a colorless solid which was redissolved in CH2Cl2 (3 ml). To this solution was added a solution of aminopyrrolidinone of Example W (200 mg, 0.68 mmol) and triethylamine (344 mg, 3.4 mmol) in CH2Cl2 (3 ml) and the resulting solution was stirred for 18 h. Removal of the solvent in vacuo and purification of the resulting solid via radial chromatography (4 mm plate) eluting with 2% EtOH/CH2Cl2 gave the title compound (223 mg, 73%) as a solid. 1H NMR (300 MHz, CDCl3) δ9.35 (1H, d), 8.68 (1H, d), 8.19 (1H, d), 7.94 (1H, d), 7.84 (1H t), 7.64 (1H, t), 7.54 (1H, t), 7.32 (1H, m), 7.19 (2H, m), 5.28 (1H, t), 4.21 (1H, m), 3.91 (1H, d), 3.78 (1H, q), 3.49 (1H, s), 1.41 (9H, s).

Workup

  1. customRemoval of the solvent in vacuo
  2. customgave a colorless solid which
  3. stirringthe resulting solution was stirred for 18 h
  4. customRemoval of the solvent
  5. customin vacuo and purification of the resulting solid via radial chromatography (4 mm plate)
  6. washeluting with 2% EtOH/CH2Cl2

Sources & evidence

ORD record
ord-1fa6bd6dffaa4b52ab6e1dc0ce97b33f
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

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