4-Fluoroaniline → HCID 46916711, compound

HRID 1507797Notes

Reaction equation

HRID 1507797 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:30])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9](S(C)=O)[S:8][C:6]=2[N:7]=1.[F:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:15][CH2:16][N:17]([C:20](=[O:30])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:18][CH2:19]2)[C:5]2[N:10]=[C:9]([NH:36][C:35]3[CH:37]=[CH:38][C:32]([F:31])=[CH:33][CH:34]=3)[S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 66758275HCID 66758275, compound

Product 1

HCID 46916711HCID 46916711, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-amino-7-[4-(4-chlorophenoxyacetyl)piperazin-1-yl]-2-methylsulfinyl-thiazolo[5,4-d]pyrimidine (47 mg, 0.1 mmol) and 4-fluoroaniline (95 μl, 1 mmol) in dioxane (5 ml) was heated under reflux for 12 hours. The reaction mixture was evaporated in vacuo and purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1/80), yielding the pure title compound (45 mg, 88%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. custompurified by flash chromatography on silica
  5. additiona mixture of methanol and dichloromethane (in a ratio of 1/80),

Sources & evidence

ORD record
ord-c2bcdf4f905443618294fd783aebab57
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

Loading…