Chlorosuccinimide → HCID 66733746, compound

HRID 1929706Notes

Reaction equation

HRID 1929706 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][CH3:18])=[N:15][CH:16]=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:29]N1C(=O)CCC1=O>CC#N.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][CH3:18])=[N:15][C:16]([Cl:29])=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 66734014HCID 66734014, compound

Product 1

HCID 66733746HCID 66733746, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 8-[2-(4-cyano-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (0.700 g; 1.840 mmol) in anhydrous MeCN (20 ml) was added dropwise, at rt, a solution of N-chlorosuccinimide (0.250 g; 1.840 mmol; 1 eq.) in anhydrous MeCN (5 ml). The resulting solution was then heated to 70° C., under nitrogen, for 4 h. Concentration to dryness afforded an oily residue which was dissolved in EA (80 ml), and this organic layer was washed with aq. sat. NaHCO3 (2×100 ml), was then dried over anh. MgSO4, filtered, and finally concentrated to dryness under reduced pressure. Purification by FC (heptane/EA=2/3) gave the expected 1-chloro-8-[2-(4-cyano-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow solid (0.417 g; 55%). LC-MS: tR=1.00 min.; [M+H]+=414.94 g/mol.

Workup

  1. concentrationConcentration to dryness
  2. customafforded an oily residue which
  3. washthis organic layer was washed with aq. sat. NaHCO3 (2×100 ml)
  4. dry with materialwas then dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationfinally concentrated to dryness under reduced pressure
  7. customPurification by FC (heptane/EA=2/3)

Sources & evidence

ORD record
ord-15631e4a6cf34b009061b357bf3c31a9
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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