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Acetic Acid → 5-Bromo-1-methyl-3-(4-(1-methylazetidin-3-yl)phenylamino)pyrazin-2(1H)-one

HRID 1919099
Notes
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Reaction equation

HRID 1919099 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=[C:17]([Br:19])[N:18]=3)=[CH:8][CH:7]=2)[CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)O[C:24](C)=O.[Na+].C=O.C(O)(=O)C>CO>[Br:19][C:17]1[N:18]=[C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([CH:4]3[CH2:5][N:2]([CH3:24])[CH2:3]3)=[CH:11][CH:10]=2)[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866612603-(4-(Azetidin-3-yl)phenylamino)-5-bromo-1-methylpyrazin-2(1H)-one Hydrochloride

Product 1

HCID 580439355-Bromo-1-methyl-3-(4-(1-methylazetidin-3-yl)phenylamino)pyrazin-2(1H)-oneYield 119.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 298c (100 mg, 0.24 mmol), NaBH(OAc)3 (100 mg, 0.48 mmol), HCHO (10 mL) and acetic acid (1 mL) in methanol (15 mL) was stirred at room temperature for 4 h. The solvent was evaporated in vacuo and the residue was neutralized with NaHCO3 solution until pH 8 was reached. The mixture was extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and concentrated under reduced pressure to give 298d (100 mg), which was used for the next step without further purification. MS: [M+H]+ 349.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b61a861fab674b8fa8efe83757f8ae8d
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618107B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes