N-Iodosuccinimide → HCID 178523380, compound

HRID 2042288Notes

Reaction equation

HRID 2042288 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C1C(=O)N([I:36])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C@H:11]3[CH2:12][CH2:13][C@H:14]([CH2:17][NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:15][CH2:16]3)=[N:9][C:10]=2[I:36])[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178523379HCID 178523379, compound

Product 1

HCID 178523380HCID 178523380, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of benzyl {[trans-4-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methyl}carbamate (1.49 g, 0.00374 mol) in DMF (0.6 mL) was added NIS (1.0 g, 0.0045 mol). The reaction mixture was stirred at 55° C. overnight then diluted with EtOAc (20 mL), washed with water (2×40 mL) and brine (20 mL), then dried over Na2SO4 and concentrated in vacuo. The crude mixture thus isolated was chromatographed over silica gel eluting with hexane→hexane:EtOAc 1:1 to afford 1.7 g of the title compound.

Workup

  1. washwashed with water (2×40 mL) and brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude mixture thus isolated
  5. customwas chromatographed over silica gel eluting with hexane→hexane:EtOAc 1:1

Sources & evidence

ORD record
ord-71ff226a496e424c9a4e6cacb7824e19
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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