Sodium Carbonate → N2-(3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropyl)-6-chloro-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

HRID 589840Notes

Reaction equation

HRID 589840 reaction equation
[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[C:4]([C:11]([NH2:13])=[O:12])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.[O:21]([CH2:39][C:40]([CH3:56])([CH3:55])[CH2:41][NH:42][C:43](=O)[O:44]C1C=CC([N+]([O-])=O)=CC=1)[Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C(#N)C>[O:21]([CH2:39][C:40]([CH3:56])([CH3:55])[CH2:41][NH:42][C:43]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([Cl:1])=[C:3]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)[C:4]([C:11]([NH2:13])=[O:12])=[C:5]2[CH2:10]1)=[O:44])[Si:22]([C:35]([CH3:38])([CH3:36])[CH3:37])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 665839426-Chloro-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamideHCID 665840014-Nitrophenyl 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylcarbamate

Product 1

HCID 86680811N2-(3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropyl)-6-chloro-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 0.250 (0.85 mmol) of 6-chloro-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide, 0.518 g (1.02 mmol) of 4-nitrophenyl 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylcarbamate and 0.235 g (1.70 mmol) of sodium carbonate in 3 ml of acetonitrile is heated at 65° C. for 1 hour 30 minutes. After cooling, the mixture is poured into aqueous 1N sodium hydroxide solution and the product is extracted with dichloromethane. After drying over sodium sulfate and filtering, the solvent is evaporated off under reduced pressure and the residue is purified by chromatography on a column of silica gel, eluting with a mixture of 35 to 65% ethyl acetate in cyclohexane, to give 0.44 g of N2-(3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropyl)-6-chloro-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a pale yellow foam.

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialAfter drying over sodium sulfate
  4. filtrationfiltering
  5. customthe solvent is evaporated off under reduced pressure
  6. customthe residue is purified by chromatography on a column of silica gel
  7. washeluting with a mixture of 35 to 65% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-41ff6053d9064e0a930cc7f5b4d1bd8a
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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