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Diisopropylethylamine → Tert-butyl 3-((7-chloropyrido[3,4-b]pyrazin-5-ylamino)methyl)-3-fluoropiperidine-1-carboxylate

HRID 57584
Notes
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Reaction equation

HRID 57584 reaction equation
[NH2:1][CH2:2][C:3]1([F:16])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.CCN(C(C)C)C(C)C.Cl[C:27]1[C:32]2=[N:33][CH:34]=[CH:35][N:36]=[C:31]2[CH:30]=[C:29]([Cl:37])[N:28]=1>C1COCC1>[Cl:37][C:29]1[N:28]=[C:27]([NH:1][CH2:2][C:3]2([F:16])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:4]2)[C:32]2=[N:33][CH:34]=[CH:35][N:36]=[C:31]2[CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 56973580tert-Butyl 3-(aminomethyl)-3-fluoropiperidine-1-carboxylateHCID 717428275,7-Dichloropyrido(3,4-b)pyrazine

Product 1

HCID 86717373Tert-butyl 3-((7-chloropyrido[3,4-b]pyrazin-5-ylamino)methyl)-3-fluoropiperidine-1-carboxylateYield 26.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

tert-butyl 3-(aminomethyl)-3-fluoropiperidine-1-carboxylate (3.86 g, 16.6 mmol) and DIPEA (3.22 g, 24.9 mmol) were added to a solution of 5,7-dichloropyrido[3,4-b]pyrazine (3.32 g, 16.6 mmol) in THF (60 mL) and the mixture was refluxed overnight. The volatile components were evaporated and the residue was extracted with ethyl acetate. Ethyl acetate was washed with brine and dried. The solvent was removed in vacuo The crude residue was purified by silica-gel chromatography eluting with Hexane-50% EtOAc/Hexane (gradient) then C18 column to afford the subtitled compound as pale yellow solid 1.76 g. MS (m/z): 396 (M+H)+

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe volatile components were evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washEthyl acetate was washed with brine
  5. customdried
  6. customThe solvent was removed in vacuo The crude residue
  7. customwas purified by silica-gel chromatography
  8. washeluting with Hexane-50% EtOAc/Hexane (gradient)

Sources & evidence

ORD record
ord-93a4037ccaae4252af2679660a6608b3
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes