Diisopropylethylamine → 1,1-Dimethylethyl (3S)-3-[[(3-amino-6-bromo-2-pyrazinyl)carbonyl]amino]-1-piperidinecarboxylate

HRID 646772Notes

Reaction equation

HRID 646772 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:45]([O:49][C:50]([N:52]1[CH2:57][CH2:56][CH2:55][C@H:54]([NH2:58])[CH2:53]1)=[O:51])([CH3:48])([CH3:47])[CH3:46]>O>[NH2:1][C:2]1[C:3]([C:9]([NH:58][C@H:54]2[CH2:55][CH2:56][CH2:57][N:52]([C:50]([O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:51])[CH2:53]2)=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 587105891,1-Dimethylethyl (3S)-3-[[(3-amino-6-bromo-2-pyrazinyl)carbonyl]amino]-1-piperidinecarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-amino-6-bromopyrazine-2-carboxylic acid (3.63 g, 16.65 mmol), HATU (9.49 g, 25.0 mg) and DIEA (4.35 mL, 25.0 mmol) was added to a solution of (s)-3-amino-piperidine-1-carboxylic acid tert-butyl ester (4.00 g, 19.97 mmol, commercially available from Astatech or Arch Corporation). It was stirred at room temperature overnight. The reaction mixture was poured into water (200 mL), and extracted with ethyl acetate (2×150 mL) then dried over anhydrous sodium sulfate and filteration, concentration and purified by column chromatography to give 1,1-dimethylethyl (3S)-3-{[(3-amino-6-bromopyrazin-2-yl)carbonyl]amino}piperidine-1-carboxylate 5.00 g (75.0% yield): MS (EI) for C15H22BrN5O3: 401.12 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. dry with materialthen dried over anhydrous sodium sulfate and filteration, concentration
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-39cdc3000770407ea2ca8f5d1c6c20cd
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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