Dichloromethane → HCID 67188173, compound

HRID 551818Notes

Reaction equation

HRID 551818 reaction equation
[N:1]1([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.ClCCl.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.Cl.Cl.[NH:38]1[CH2:42][CH2:41][CH:40]([C:43]2[CH:44]=[N:45][NH:46][CH:47]=2)[CH2:39]1>C(N(CC)CC)C>[NH:45]1[CH:44]=[C:43]([CH:40]2[CH2:41][CH2:42][N:38]([C:28]([N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]([C:11]4[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=4)[CH2:2][CH2:3]3)=[O:34])[CH2:39]2)[CH:47]=[N:46]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 94429TriphosgeneHCID 671872291000688-81-2HCID 67190045HCID 67190045, compound

Product 1

HCID 67188173HCID 67188173, compoundYield 242.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Conditions

Temperature
4 °C

Procedure

2.7 g of methyl 4-(3,4-dihydroquinoxalin-1(2H)-yl)benzoate and 50 ml of dichloromethane are introduced into a three-necked flask equipped with a magnetic stirrer and placed under an inert atmosphere. After cooling to 4° C., 4.2 ml of triethylamine and 1.19 g of triphosgene are successively added. The reaction medium is stirred at ambient temperature for 4 h. 2.11 g of 4-(pyrrolidin-3-yl)-1H-pyrazole dihydrochloride and 1.4 ml of triethylamine are then introduced and the mixture is stirred at ambient temperature for 18 h. The reaction medium is washed with a saturated aqueous sodium hydrogencarbonate solution; the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a gradient of methanol from 1.5% to 3% in dichloromethane. 4.2 g of methyl 4-[4-{[3-(1H-pyrazol-4-yl)pyrrolidin-1-yl]carbonyl}-3,4-dihydroquinoxalin-1(2H)-yl]benzoate are obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. stirringthe mixture is stirred at ambient temperature for 18 h
  3. washThe reaction medium is washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluted with a gradient of methanol from 1.5% to 3% in dichloromethane

Sources & evidence

ORD record
ord-e8b97dc7a10041cfaf52031ab8302a07
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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