N-Iodosuccinimide → HCID 86697432, compound

HRID 1478263Notes

Reaction equation

HRID 1478263 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-b92e4cbe69cd4f51919897fb2579e0e5
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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