N-Iodosuccinimide → HCID 58177409, compound

HRID 1916126Notes

Reaction equation

HRID 1916126 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14]([S:35]([CH3:38])(=[O:37])=[O:36])[N:13]=2)[CH2:6]1)(=[O:4])=[O:3].[I:39]N1C(=O)CCC1=O>CC(C)=O>[I:39][C:26]1[C:20]2[C:21](=[N:22][CH:23]=[C:18]([C:17]3[C:12]([NH:11][C@H:7]4[CH2:8][CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:6]4)=[N:13][C:14]([S:35]([CH3:38])(=[O:36])=[O:37])=[N:15][CH:16]=3)[N:19]=2)[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:34])[CH3:32])[CH:25]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58177355HCID 58177355, compound

Product 1

HCID 58177409HCID 58177409, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methanesulfonyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine derived from Example 84, step 1 (70 mg, 0.12 mmol) in acetone (0.5 ml) was treated with N-Iodosuccinimide (41 mg, 0.18 mmol) and stirred at 20° C. for 16 hours. The crude reaction mixture was concentrated in vacuo and was purified by silica gel chromatography (0% to 40% ethyl acetate/dichloromethane) to give 67 mg (79%) of {5-[7-Iodo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2-methanesulfonyl-pyrimidin-4-yl}-((S)-1-methanesulfonyl-piperidin-3-yl)-amine. MS (ES+): 708.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customwas purified by silica gel chromatography (0% to 40% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-21b35c679643425abebe64e3d969b542
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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