Pyridine → HCID 86756036, compound

HRID 1857501Notes

Reaction equation

HRID 1857501 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:17])=[CH:13][C:14]=2[NH2:16])[C@H:9]([N:18]([CH2:23][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:8][C@@H:7]1[CH3:38])=[O:5])[CH3:2].ClCCl.N1C=CC=CC=1.Cl[C:49]([O:51][CH3:52])=[O:50]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:17])=[CH:13][C:14]=2[NH:16][C:49]([O:51][CH3:52])=[O:50])[C@H:9]([N:18]([CH2:23][C:24]2[CH:25]=[C:26]([C:34]([F:37])([F:35])[F:36])[CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:8][C@@H:7]1[CH3:38])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 86756035HCID 86756035, compound

Product 1

HCID 86756036HCID 86756036, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a pre-dried flask under nitrogen atmosphere was added cis-8-amino-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-chloro-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 109) (30 mg, 0.053 mmol), followed by anhydrous dichloromethane (2 mL), pyridine (0.5 mL), and methyl chloroformate (0.016 mL, 0.21 mmol). The reaction was stirred overnight at room temperature before ethyl acetate was added, and the mixture was extracted three times with 1N HCl, followed by brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the desired product (29 mg, 87%). MS m/z 626 (M+ +H); 1H NMR (CDCl3) δ 7.82 (bs, 1H), 7.8 (bs, 1H), 7.7 (bs, 1H), 6.68 (bs, 1H), 6.7 (bs, 1H), 3.8 (s, 3H), 3.75 (s, 3H).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted three times with 1N HCl
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-664d2caca69f44c584107951a4098553
Source dataset
uspto-grants-2000_11
Patent number
US06147090

Reaction notes

Loading…