4-Fluoroaniline → HCID 46916711, compound

HRID 718247Notes

Reaction equation

HRID 718247 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-4af1b8c3f6d741e19232a6299e13ac2a
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

Loading…