Dichloromethane → HCID 67189427, compound

HRID 551799Notes

Reaction equation

HRID 551799 reaction equation
[N:1]1(NC(O)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.C(N([CH:21]([CH3:23])[CH3:22])CC)(C)C.ClC(Cl)([O:27][C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[NH:36]1[CH2:40][CH2:39][CH:38]([C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)[CH2:37]1.[C:47](=[O:50])([O-])O.[Na+].Cl[CH2:53]Cl>>[N:43]1[CH:44]=[CH:45][CH:46]=[C:41]([CH:38]2[CH2:39][CH2:40][N:36]([C:47]([N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]([C:28]([O:34][C:21]([CH3:23])([CH3:53])[CH3:22])=[O:27])[CH2:2][CH2:3]3)=[O:50])[CH2:37]2)[CH:42]=1

Participants

7

Reactant 6

HCID 6344DichloromethaneHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 67190746HCID 67190746, compound

Product 1

HCID 67189427HCID 67189427, compound

Procedure

2.75 g of the tert-butyl ester of 3,4-dihydro-1(2H)-quinoxalinecarbamic acid, 117 ml of dichloromethane and 5.8 ml of diisopropylethylamine are placed in a 500 ml round-bottomed flask under a nitrogen atmosphere. 1.74 g of triphosgene are added at 0° C. and then the reaction mixture is left stirring at ambient temperature for three hours. 2 ml of diisopropylethylamine and 1.83 g of 3-(pyrrolidin-3-yl)pyridine are subsequently added and the reaction mixture is stirred for eighteen hours. 200 ml of a saturated aqueous sodium hydrogencarbonate solution are added and then the aqueous phase is extracted three times with dichloromethane. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture. 3.72 g of tert-butyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydroquinoxaline-1(2H)-carboxylate are obtained.

Workup

  1. waitthe reaction mixture is left
  2. stirringthe reaction mixture is stirred for eighteen hours
  3. extractionthe aqueous phase is extracted three times with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture

Sources & evidence

ORD record
ord-9b2f2cf246a94c50b4abf820f6011b80
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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