Trifluoroacetic acid → HCID 90082844, compound

HRID 2276874Notes

Reaction equation

HRID 2276874 reaction equation
[C:1]([C:3]1[CH:28]=[C:27]([O:29][CH3:30])[C:6]2[NH:7][C:8](=[O:26])[CH:9]([NH:18]C(=O)OC(C)(C)C)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:18][CH:9]1[C:8](=[O:26])[NH:7][C:6]2[C:27]([O:29][CH3:30])=[CH:28][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 90082820HCID 90082820, compound

Product 1

HCID 90082844HCID 90082844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 7-cyano-9-methoxy-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate (0.441 g, 1.086 mmol) was dissolved in DCM (4 ml) and TFA (1 ml, 12.98 mmol) and stirred at room temperature for 1.5 h. TFA (1 ml, 12.98 mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was concentrated, then dissolved in EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted twice more, then the organic layers were dried with Na2SO4 and evaporated. The residue was purified silica gel chromatography (DCM/MeOH). The fractions containing product were evaporated, then the material was triturated with EtOAc to give 3-amino-9-methoxy-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepine-7-carbonitrile (Intermediate B-19). 1H NMR (400 MHz, chloroform-d) δ 7.54-7.45 (m, 3H), 7.42-7.37 (m, 2H), 7.26 (d, J=1.8 Hz, 1H), 7.22 (d, J=1.5 Hz, 1H), 4.46 (s, 1H), 4.01 (s, 3H), 2.45 (br. s., 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous layer was extracted twice more
  5. dry with materialthe organic layers were dried with Na2SO4
  6. customevaporated
  7. customThe residue was purified silica gel chromatography (DCM/MeOH)
  8. additionThe fractions containing product
  9. customwere evaporated
  10. customthe material was triturated with EtOAc

Sources & evidence

ORD record
ord-4e6be7a38c4248908e70e4d7cfbf4a4c
Source dataset
uspto-grants-2015_09
Patent number
US09133139B2

Reaction notes

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