Water → HCID 86680823, compound

HRID 589894Notes

Reaction equation

HRID 589894 reaction equation
Cl.[Cl:2][C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[C:5]([C:12]([NH2:14])=[O:13])[C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1.[N+](C1C=CC([N:31]([CH:35]2[CH2:40][CH2:39][C:38](=[N:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:37][CH2:36]2)[C:32](=O)[O-:33])=CC=1)([O-])=O.C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C>[Cl:2][C:3]1[N:7]2[CH2:8][CH2:9][N:10]([C:32]([NH:31][CH:35]3[CH2:40][CH2:39][C:38](=[N:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:37][CH2:36]3)=[O:33])[CH2:11][C:6]2=[C:5]([C:12]([NH2:14])=[O:13])[C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 86680824HCID 86680824, compoundHCID 86762568HCID 86762568, compound

Product 1

HCID 86680823HCID 86680823, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 0.27 (0.82 mmol) of 6-chloro-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide hydrochloride, 0.37 g (1.06 mmol) of 4-nitrophenyl[4-[(1,1-dimethylethoxy)imino]cyclohexyl]-carbamate and 0.33 g (2.45 mmol) of sodium carbonate in 30 ml of acetonitrile is heated at 60° C. for 3 hours. After cooling, the mixture is poured into water and the product is extracted with dichloromethane. After drying over sodium sulfate and filtration, the solvent is evaporated off under reduced pressure and the residue is purified by chromatography on a column of 40 g of silica gel, eluting with a mixture of dichloromethane/ethyl acetate (60/40 to 20/80), to give 0.18 g of 6-chloro-7-(3-fluorophenyl)-N2-[4-[(1,1-dimethylethoxy)imino]cyclohexyl]-3,4-dihydropyrrolo-[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a yellowish powder, after evaporating the fractions down to a small volume of solvent, filtering off the crystallized product, washing with ethyl acetate and drying under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialAfter drying over sodium sulfate and filtration
  4. customthe solvent is evaporated off under reduced pressure
  5. customthe residue is purified by chromatography on a column of 40 g of silica gel
  6. washeluting with a mixture of dichloromethane/ethyl acetate (60/40 to 20/80)

Sources & evidence

ORD record
ord-de01748e596a4a5f82e9abce092a7ce7
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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