Chlorosuccinimide → HCID 68887671, compound

HRID 857891Notes

Reaction equation

HRID 857891 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][C:16]([C:17](=[O:19])[NH2:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26]N1C(=O)CCC1=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:15]([Cl:26])[C:16]([C:17](=[O:19])[NH2:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68887618HCID 68887618, compound

Product 1

HCID 68887671HCID 68887671, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-carbamoyl-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (8.0 g, Reference Example 3) in dichloromethane (300 mL) was treated with N-chlorosuccinimide (3.12 g). After stirring at room temperature for a further 16 hours the reaction mixture was washed four times with water (50 mL) and then once with brine (50 mL). The organic phase was then dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and pentane (3:7, v/v) to give the title compound (4.3 g) as a white solid, m.p. 183–185° C. 1H NMR [(CD3)2SO]: δ 7.52–7.40 (m, 5H), 7.30 (bs, 1H), 6.80 (bs, 1H), 4.81 (s, 2H), 3.82 (t, 2H), 3.66 (t, 2H), 1.43 (s, 9H).

Workup

  1. washwas washed four times with water (50 mL)
  2. dry with materialThe organic phase was then dried over magnesium sulfate
  3. customevaporated
  4. additionThe residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and pentane (3:7

Sources & evidence

ORD record
ord-25aebc77ef0141c0ab0a55b58c625eb0
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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