Triethylamine → HCID 66653126, compound

HRID 535448Notes

Reaction equation

HRID 535448 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2.[O:25]=[C:26]1[C:31]2[CH:32]=[C:33]([C:36](O)=[O:37])[CH:34]=[CH:35][C:30]=2[N:29]=[C:28]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:27]1>ClC(Cl)C>[CH3:8][O:9][C:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([C:36]([C:33]2[CH:34]=[CH:35][C:30]3[N:29]=[C:28]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:27][C:26](=[O:25])[C:31]=3[CH:32]=2)=[O:37])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134001251-Methoxy-2-phenylindolizineHCID 66653415HCID 66653415, compound

Product 1

HCID 66653126HCID 66653126, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

2.25 ml (16.12 mmol) of triethylamine and 3 g (13.44 mmol) of 1-methoxy-2-phenylindolizine (according to the method described in WO 03/084956) diluted in 20 ml of dichloroethane are added, under an inert atmosphere at ambient temperature, to 4.22 g (14.78 mmol) of 4-oxo-2-phenyl-4H-3,1-benzoxazine-6-carboxylic acid (described in WO 06/097625) in 100 ml of dichloroethane. After stirring overnight at ambient temperature, the reaction medium is filtered, and rinsed with dichloroethane. The filtrate is washed with water, dried over sodium sulphate, filtered, and concentrated under reduced pressure. The residue is filtered through a silica pâté, elution being carried out with dichloromethane. 4.4 g of a yellow solid are obtained.

Workup

  1. filtrationthe reaction medium is filtered
  2. washrinsed with dichloroethane
  3. washThe filtrate is washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe residue is filtered through a silica pâté
  8. washelution

Sources & evidence

ORD record
ord-2a3bf76650df4f01af2e44ce62e3f122
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

Loading…