HCID 21265977, compound → 5-(2-fluoro-phenyl)-3H-thieno[2,3-e][1,4]diazepin-2-ylamine

HRID 566272Notes

Reaction equation

HRID 566272 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[N:8][CH2:9][C:10]#[N:11]>C(O)(=O)C>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[N:1]=[C:10]([NH2:11])[CH2:9][N:8]=1

Participants

3

Reactant 1

HCID 21265977HCID 21265977, compound

Product 1

HCID 212660085-(2-fluoro-phenyl)-3H-thieno[2,3-e][1,4]diazepin-2-ylamineYield 24.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 70 g of [(2-amino-thiophen-3-yl)-(2-fluoro-phenyl)-methyleneamino]acetonitrile in 980 ml of acetic acid was stirred at 65° C. under argon for 1.5 h. After cooling the solvent was removed in a vacuum, the residue was dissolved in dichloromethane and neutralized with sodium bicarbonate solution while cooling with ice and extracted. The dichloromethane extracts were dried with sodium sulphate, filtered and evaporated to dryness in a vacuum. After crystallization from dichloromethane there were obtained 17.1 g of 5-(2-fluoro-phenyl)-3H-thieno[2,3-e][1,4]diazepin-2-ylamine of m.p. 219-220° C. (dec.).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed in a vacuum
  3. dissolutionthe residue was dissolved in dichloromethane and neutralized with sodium bicarbonate solution
  4. temperaturewhile cooling with ice
  5. extractionextracted
  6. dry with materialThe dichloromethane extracts were dried with sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness in a vacuum
  9. customAfter crystallization from dichloromethane

Sources & evidence

ORD record
ord-6558805d5fed41a9afbab82b6dfa0720
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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