Water → HCID 58316971, compound

HRID 1187309Notes

Reaction equation

HRID 1187309 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:22])[C:9]2[C:17]3[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25].I(C1C=CC=CC=1C(O)=O)(=O)=O.O>CS(C)=O>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[O:22])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 58317009HCID 58317009, compound

Product 1

HCID 58316971HCID 58316971, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(4-isopropylamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (78, 102 mg, 0.242 mmol) in 1 mL of dimethylsulfoxide, stabilized 2-iodoxybenzoic acid (181 mg, 45%, 0.29 mmol) is added and the reaction is stirred at room temperature for 1 hour. The reaction is poured into water and stirred for 30 minutes, and the precipitate is collected by filtration. The resulting solid is dissolved in 2 mL of tetrahydrofuran and purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to give the desired compound (P-1106, 34 mg). MS (ESI) [M+H+]+=420.0.

Workup

  1. additionis added
  2. stirringstirred for 30 minutes
  3. filtrationthe precipitate is collected by filtration
  4. dissolutionThe resulting solid is dissolved in 2 mL of tetrahydrofuran
  5. custompurified by silica gel column chromatography
  6. washeluting with ethyl acetate and dichloromethane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7c931be00c894b8a993f8a70142ed9e4
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

Loading…