Dichloromethane → HCID 71554404, compound

HRID 1776440Notes

Reaction equation

HRID 1776440 reaction equation
[CH2:1]([O:3][C:4]1[CH:37]=[C:36]([F:38])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:21]([O:31][CH2:32][CH2:33][S:34][CH3:35])=[CH:20][N:19]=3)=[N:10]2)=[C:6]([F:39])[CH:5]=1)[CH3:2].ClC1C=CC=CC=1C(OO)=[O:48].ClCCl.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([F:39])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[C:21]([O:31][CH2:32][CH2:33][S:34]([CH3:35])=[O:48])=[CH:20][N:19]=3)=[N:10]2)=[C:36]([F:38])[CH:37]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 125873982-Chlorobenzene-1-carboperoxoic acidHCID 86732468HCID 86732468, compound

Product 1

HCID 71554404HCID 71554404, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.24 g 2-[1-(4-ethoxy-2,6-difluorobenzyl)-1H-indazol-3-yl]-5-[2-(methylsulfanyl)ethoxy]-N-(pyridin-4-yl)pyrimidin-4-amine (4-16, 2.26 mmol, 1. eq.) in 2.15 ml of dry chloroform, was added slowly at 0° C. a solution of 557 mg 2-chlorobenzenecarboperoxoic acid (77%, 2.49 mmol, 1.1 eq.) in 2.15 ml chloroform. After 30 min dichloromethane and sodium thiosulfate-solution (10%) were added. The slurry was stirred for 5 min. After separating the solid (product) the aqueous layer was washed with dichloromethane twice. The organic layers were dried with sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography and combined the former isolated solid to yield 1.22 g (2.05 mmol, 91%) of the analytically pure target compound.

Workup

  1. customAfter separating the solid (product) the aqueous layer
  2. washwas washed with dichloromethane twice
  3. dry with materialThe organic layers were dried with sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. customformer isolated solid
  7. customto yield 1.22 g (2.05 mmol, 91%) of the analytically pure target compound

Sources & evidence

ORD record
ord-d065e187502845d7b5999bc5fbe77b52
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

Loading…