Methyl chloroformate → HCID 118045457, compound

HRID 595809Notes

Reaction equation

HRID 595809 reaction equation
[Br:1][C:2]1[C:3]([NH2:14])=[N:4][CH:5]=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[N:7]=1.CCN(C(C)C)C(C)C.Cl[C:25]([O:27][CH3:28])=[O:26]>C(Cl)Cl>[NH2:14][C:3]1[N:4]=[CH:5][C:6]([CH:8]2[CH2:9][CH2:10][N:11]([C:25]([O:27][CH3:28])=[O:26])[CH2:12][CH2:13]2)=[N:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 118045729HCID 118045729, compound

Product 1

HCID 118045457HCID 118045457, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-(piperidin-4-yl)pyrazin-2-amine (60 mg, 0.233 mmol) in DCM (2 mL) in ice bath was added DIEA (408 μl, 2.333 mmol) and methyl chloroformate (18.07 μl, 0.233 mmol). The reaction mixture was stirred under ice bath for 30 min. The reaction mixture was partitioned between DCM and water. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered off, and evaporated in vacuo. The crude methyl 4-(5-amino-6-bromopyrazin-2-yl)piperidine-1-carboxylate was used for next step. LCMS (m/z): 315.0/317.0 (MH+), 0.647 min.

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. customevaporated in vacuo
  7. custom315.0/317.0 (MH+), 0.647 min.

Sources & evidence

ORD record
ord-a4b7dbfdec03499ba50a3cb2132d47bf
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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