Pyridine → HCID 57500341, compound

HRID 2273525Notes

Reaction equation

HRID 2273525 reaction equation
N1C=CC=CC=1.Cl[C:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:9].[CH2:27]([O:34][C:35]1[C:43]2[N:39]([CH:40]=[C:41]([CH3:46])[C:42]=2[O:44][CH3:45])[CH:38]=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.C(O)C>[CH2:27]([O:34][C:35]1[C:43]2[N:39]([C:40]([C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:14]([CH:19]=3)[C:15]([O:17][CH3:18])=[O:16])=[O:9])=[C:41]([CH3:46])[C:42]=2[O:44][CH3:45])[CH:38]=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 57500340HCID 57500340, compoundHCID 57500342HCID 57500342, compound

Product 1

HCID 57500341HCID 57500341, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

4.4 ml (54.3 mmol) of pyridine and then 15.0 g (48.4 mmol) of methyl 5-(chlorocarbonyl)-2-[(trifluoro-acetyl)amino]benzoate (described in Patent Application WO2003084956) are added, under argon, to the solution of 13.2 g (49.4 mmol) of 8-(benzyloxy)-1-methoxy-2-methylindolizine in 165 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 3 hours. This is diluted with dichloromethane and this organic solution is washed with a saturated aqueous solution of sodium bicarbonate and then a saturated aqueous solution of sodium chloride, and dried over sodium sulphate. After concentration under reduced pressure, the solid obtained is taken up in ethanol, filtered and washed with ethanol, to give 16.2 g (61%) of an orange powder.

Workup

  1. washthis organic solution is washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materiala saturated aqueous solution of sodium chloride, and dried over sodium sulphate
  3. concentrationAfter concentration under reduced pressure
  4. customthe solid obtained
  5. filtrationfiltered
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-4c92311c560946f69d000af38d5cc00d
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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