4-Trifluoromethyl-1,2-phenylenediamine → HCID 178516957, compound

HRID 1716325Notes

Reaction equation

HRID 1716325 reaction equation
[O:1]=[C:2]1[CH:8]([S:9]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[O:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[F:40][C:41]([F:51])([F:50])[C:42]1[CH:43]=[C:44]([NH2:49])[C:45]([NH2:48])=[CH:46][CH:47]=1.OS([O-])=O.[Na+]>CCO>[F:40][C:41]([F:50])([F:51])[C:42]1[CH:47]=[CH:46][C:45]2[NH:48][C:16]([C:15]3[CH:14]=[CH:13][C:12]([S:9]([CH:8]4[CH2:7][CH2:6][CH2:5][CH2:4][N:3]([O:20][C:21]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:2]4=[O:1])(=[O:11])=[O:10])=[CH:19][CH:18]=3)=[N:49][C:44]=2[CH:43]=1

Participants

5

Reactant 3

HCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 23665763Sodium BisulfiteHCID 86619942HCID 86619942, compound

Product 1

HCID 178516957HCID 178516957, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Oxo-1-trityloxy-azepane-3-sulfonyl)-benzaldehyde prepared from step G (17.4 mg, 0.0322 mmol) and 4-Trifluoromethyl-benzene-1,2-diamine (23.6 mg, 0.13 mmol) in 5.0 ml of anhydrous EtOH was heated to reflux and a 1.2 ml aqueous solution of NaHSO3 (100.1 mg) was added in one portion. The resulting solution was stirred and heated to reflux for overnight. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc and water. The organic phase was washed sequentially with water and saturated NaCl solution, and then dried over anhydrous Na2SO4. The EtOAc solution was concentrated under reduced pressure to give a crude material, which was then purified by a column chromatography (0˜10% EtOAc in hexane and dichloromethane 1:1). MS: 696.2 (M+H)+.

Workup

  1. temperatureto reflux
  2. temperatureheated
  3. temperatureto reflux for overnight
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additiondiluted with EtOAc and water
  6. washThe organic phase was washed sequentially with water and saturated NaCl solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationThe EtOAc solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e554e3f4524a414f93133aa97df79c78
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

Loading…