HCID 89832300, compound → HCID 86762237, compound

HRID 1619038Notes

Reaction equation

HRID 1619038 reaction equation
C([N:4]1[CH2:12][CH:11]2[C:6]([C:22]3[S:23][C:24]([F:27])=[CH:25][CH:26]=3)([N:7]=[C:8]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:9][CH2:10]2)[CH2:5]1)C=C>C(Cl)(Cl)Cl.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:27][C:24]1[S:23][C:22]([C:6]23[CH2:5][NH:4][CH2:12][CH:11]2[CH2:10][S:9][C:8]([NH:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7]3)=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 89832300HCID 89832300, compound

Product 1

HCID 86762237HCID 86762237, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Through a stirred solution of racemic N-[6-allyl-7a-(5-fluoro-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (163 mg, 0.406 mmol) in chloroform (4.1 mL) is passed a stream of nitrogen for 20 minutes. N,N-Dimethylbarbituric acid (380 mg, 2.44 mmol) is added and degassing is continued for a further 5 minutes. Tetrakis(triphenylphosphine)palladium (70 mg, 0.061 mmol) is added and the mixture is stirred under nitrogen at room temperature for 45 minutes. The mixture is diluted with dichloromethane (approximately 15 mL) and extracted twice with 1 M hydrochloric acid (10 mL). The pH of the combined aqueous acid extracts is adjusted with 5 M sodium hydroxide (5 mL). The aqueous solution is extracted three times with dichloromethane (20 mL) and the combined dichloromethane extracts are dried over sodium sulfate, filtered, and concentrated to give the title compound (135 mg, 92%). ES/MS (m/e): 361 (M+H).

Workup

  1. customfor 20 minutes
  2. customdegassing
  3. extractionextracted twice with 1 M hydrochloric acid (10 mL)
  4. extractionThe aqueous solution is extracted three times with dichloromethane (20 mL)
  5. dry with materialthe combined dichloromethane extracts are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e45e25f7d29404ba0e89a0b9c27370e
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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