Sulfolane → 6,11-Dihydro-7-hydroxy-2-(trifluoromethyl)-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 1691424Notes

Reaction equation

HRID 1691424 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Cl[C:11]1[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14].S1(CCCC1)(=O)=O>O>[OH:9][C:3]1[C:2]2[NH:1][C:13](=[O:14])[C:12]3[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:21])[F:22])=[N:19][C:11]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 5799372,3-DiaminophenolHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 669016696,11-Dihydro-7-hydroxy-2-(trifluoromethyl)-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,3-diaminophenol (79 g, 0.64 mol), 2-chloro-6-(trifluoromethyl)nicotinic acid (100 g, 0.44 mol) and sulfolane (1 L) was heated under nitrogen at 150° C. overnight. After cooling to rt, the reaction mixture was poured into water. The precipitate was collected by filtration, and was re-dissolved in EtOAc, washed with water and brine, dried over MgSO4, filtered and concentrated to give 7-hydroxy-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe precipitate was collected by filtration
  3. dissolutionwas re-dissolved in EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aaf4f17719cc4809b94fe37e85d0708c
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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