Hydrochloric Acid → 12-amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

HRID 649952Notes

Reaction equation

HRID 649952 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:3]=1[NH:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14]#[N:15].Cl>CO.O>[NH2:15][C:14]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[S:9][C:5]=2[NH:4][C:3]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 184222672-(2-Amino-5-fluoroanilino)benzo[b]thiophene-3-carbonitrile

Product 1

HCID 1842238512-amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(2-Amino-5-fluoroanilino)benzo[b]thiophene-3-carbonitrile (155 g) was suspended in a mixture of methanol (250 ml) and water (200 ml) and 35% aqueous hydrochloric acid (42 ml) was added. The mixture was stirred under reflux with heating for 5.5 hours. The reaction mixture was cooled and stirred at 20° C. for 1 hour. The precipitated crystals were filtered by suction, washed successsively with water (500 ml) and isopropyl alcohol (200 ml) and dried in a drying box overnight to give 12-amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine.1 hydrochloride (104 g) as yellow crystals.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperaturewith heating for 5.5 hours
  4. temperatureThe reaction mixture was cooled
  5. stirringstirred at 20° C. for 1 hour
  6. filtrationThe precipitated crystals were filtered by suction
  7. washwashed successsively with water (500 ml) and isopropyl alcohol (200 ml)
  8. customdried in a drying box overnight

Sources & evidence

ORD record
ord-13029e12ed1b4a8a874254c2bb22fa3b
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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