Water → 7-cyano-8-iodo-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid 2-tert-butyl ester

HRID 857898Notes

Reaction equation

HRID 857898 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([C:17]#[N:18])[CH:16]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:25]NC(=O)CCC(N)=O.O.C(OCC)(=O)C>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([C:17]#[N:18])[C:16]([I:25])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21864724N-IodosuccinamideHCID 688869257-cyano-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester

Product 1

HCID 688913777-cyano-8-iodo-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid 2-tert-butyl esterYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-cyano-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (8.6 g, Reference Example 4(b)) in dry dimethylformamide (80 mL) was treated with N-iodosuccinamide (6.07 g) over 10 minutes. After stirring at room temperature for a further 4 hours the reaction mixture was treated with water and ethyl acetate. The organic phase was separated, further washed with water, then dried over magnesium sulfate and evaporated. The residue was triturated with diethyl ether to give the title compound (7.50 g) as a buff solid, m.p. 174–178° C. 1H NMR [(CD3)2SO]: δ 7.58–7.48 (m, 5H), 4.43 (s, 2H), 3.97 (t, 2H), 3.65 (t, 2H) and 1.46 (s, 9H).

Workup

  1. customThe organic phase was separated
  2. washfurther washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-5d5a1d9a49b64f0e91b2bec8f0339139
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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