Water → (S)-8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

HRID 1378169Notes

Reaction equation

HRID 1378169 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>O1CCOCC1.N1C=CC=CC=1>[Br:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 22876620(S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Product 1

HCID 53644483(S)-8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 12.8 g (35.4 mmol) of (S)-8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxamide in a mixture of 50 ml of dioxan and 7 ml of pyridine was treated at 7 to 10° with 6.5 ml of trifluoroacetic anhydride. The suspension was stirred at room temperature for 2.5 hours and poured into 200 ml of water. After 1 hour the suspension was suction filtered. There were obtained 12.1 g (100%) of (S)-8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile of m.p. 253°-254°.

Workup

  1. waitAfter 1 hour the suspension was
  2. filtrationsuction filtered

Sources & evidence

ORD record
ord-ca2f21d9bf634837b2ebebfb3d735adf
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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