Thiophosgene → HCID 54130839, compound

HRID 1858082Notes

Reaction equation

HRID 1858082 reaction equation
C(=O)([O-])[O-].[Ca+2].[C:6](Cl)(Cl)=[S:7].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[CH2:23][CH2:24][O:25][C:26]1[C:35]2[C:30](=[CH:31][C:32]([Cl:37])=[C:33]([NH2:36])[CH:34]=2)[NH:29][C:28](=[O:38])[C:27]=1[C:39]1[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([CH3:46])[CH:40]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>O.C(Cl)(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[CH2:23][CH2:24][O:25][C:26]1[C:35]2[C:30](=[CH:31][C:32]([Cl:37])=[C:33]([N:36]=[C:6]=[S:7])[CH:34]=2)[NH:29][C:28](=[O:38])[C:27]=1[C:39]1[CH:40]=[C:41]([CH3:46])[CH:42]=[C:43]([CH3:45])[CH:44]=1)=[O:16])([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 54025520HCID 54025520, compound

Product 1

HCID 54130839HCID 54130839, compound

Reagents, catalysts & solvents 1

HCID 22418719Chloroform waterSolvent

Procedure

To a stirred suspension of calcium carbonate (320 mg) and thiophosgene (120 mg) in 10 mL water:chloroform (1:1) at 0° C. was added 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (450 mg, prepared essentially as described in Example 1) and the mixture stirred at low temperature. After 2 hours the reaction was quenched by the addition of 10% hydrochloric acid and stirring continued until the gas evolution ceased. The mixture was then extracted with chloroform, the combined organics dried over magnesium sulfate and concentrated in vacuo to provide the crude title compound (480 mg).

Workup

  1. customprepared essentially
  2. customAfter 2 hours the reaction was quenched by the addition of 10% hydrochloric acid
  3. stirringstirring
  4. extractionThe mixture was then extracted with chloroform
  5. dry with materialthe combined organics dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a09545b6299460d84f53035fa6b2bb0
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

Loading…