N-Iodosuccinimide → HCID 178523380, compound

HRID 449000Notes

Reaction equation

HRID 449000 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([Cl:27])[C:21]3=[CH:20][N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([I:36])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([Cl:27])[C:21]3=[C:20]([I:36])[N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH: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. MS (ES+): m/z 525.01 [MH+].

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-b06fad7772f44560b39ce2e5db1b3c37
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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