N-Iodosuccinimide → HCID 86697432, compound

HRID 1844344Notes

Reaction equation

HRID 1844344 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([NH:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:9][C:4]2=[CH:3][CH:2]=1.C1C(=O)N([I:31])C(=O)C1>CN(C=O)C>[I:31][C:3]1[CH:2]=[N:1][N:5]2[CH:6]=[CH:7][C:8]([NH:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:9][C:4]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86697431HCID 86697431, compound

Product 1

HCID 86697432HCID 86697432, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (S)-tert-butyl 2-((pyrazolo[1,5-a]pyrimidin-5-ylamino)methyl)pyrrolidine-1-carboxylate (790 mg, 2.490 mmol) was dissolved in 10 mL of DMF, was added NIS (617 mg, 2.740 mmol). This mixture is stirred for 4 hr at rt, and then quenched with 10 mL of water. It was then diluted with 50 mL EtOAc and the organic layer was separated, washed twice with brine, and dried over MgSO4. It was concentrated and purified on the silica gel eluting with 20-100% EtOAc/hex to obtain 1.03 g (93%) an off-white solid.

Workup

  1. customquenched with 10 mL of water
  2. additionIt was then diluted with 50 mL EtOAc
  3. customthe organic layer was separated
  4. washwashed twice with brine
  5. dry with materialdried over MgSO4
  6. concentrationIt was concentrated
  7. custompurified on the silica gel eluting with 20-100% EtOAc/hex

Sources & evidence

ORD record
ord-2df2ae57c93441e1aeb8b0ab8eb4a366
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

Loading…