N-bromobutanimide → HCID 89739210, compound

HRID 2206590Notes

Reaction equation

HRID 2206590 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[Br:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 50986448Tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 89739210HCID 89739210, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylate (1.9 g, 8 mmol) in N,N-dimethylformamide (20 ml) was added dropwise 1-bromopyrrolidine-2,5-dione (1.4 g, 8 mmol) at 0° C. The reaction was allowed to stirred for 4 h at rt. The reaction mixture was quenched with water (30 mL), and extracted with acetic ester (30 mL×3). The combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph silica gel (elute: petroleum ether/ethyl acetate=1:1) to give tert-butyl 4-(6-amino-5-bromopyridin-2-yl)piperazine-1-carboxylate (0.2 g, 8.2%) as a yellow solid. LCMS (M+H) m/z: calcd. 356.08. found 357.

Workup

  1. customThe reaction mixture was quenched with water (30 mL)
  2. extractionextracted with acetic ester (30 mL×3)
  3. dry with materialThe combined organic phase was dried by anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatograph silica gel (elute: petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d2b9ba550d2b48b7b5d9eb70216bb8d2
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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