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Trifluoroacetic acid → 5-Bromo-3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]pyrazin-2-amine

HRID 81376
Notes
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Reaction equation

HRID 81376 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[N:10]=[C:11]([C:30]#[CH:31])[C:12]([N:15](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:13][CH:14]=1.[Cl:32][CH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38](Cl)=[N:39][OH:40])=[CH:36][CH:35]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:8][C:9]1[N:10]=[C:11]([C:30]2[O:40][N:39]=[C:38]([C:37]3[CH:42]=[CH:43][C:34]([CH2:33][Cl:32])=[CH:35][CH:36]=3)[CH:31]=2)[C:12]([NH2:15])=[N:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 58070394tert-butyl N-(5-bromo-3-ethynylpyrazin-2-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 766866014-(Chloromethyl)-N-hydroxybenzimidoyl chloride

Product 1

HCID 580703405-Bromo-3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (330.3 mg, 455.0 μL, 3.264 mmol) was added to a solution of tert-butyl N-(5-bromo-3-ethynyl-pyrazin-2-yl)-N-tert-butoxycarbonyl-carbamate (1000 mg, 2.511 mmol) and 4-(chloromethyl)-N-hydroxy-benzimidoyl chloride 6 (563.6 mg, 2.762 mmol) in DCM (7 mL). The mixture was stirred at RT overnight. The reaction mixture was partitioned between DCM and water and the organic extract was dried (MgSO4) and concentrated in vacuo yielding an oil that was dissolved in DCM (10 mL). TFA (2 mL) was added and the mixture was stirred at RT for 15 min before being concentrated in vacuo. MS (ES−) 364

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. extractionthe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customyielding an oil that
  6. stirringthe mixture was stirred at RT for 15 min
  7. concentrationbefore being concentrated in vacuo

Sources & evidence

ORD record
ord-a35c28bbddcd41b9ab43dcc9f75b3000
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846686B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes