Water → HCID 53807155, compound

HRID 1378014Notes

Reaction equation

HRID 1378014 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([NH2:17])=O)=[C:10]3[C@@H:9]3[CH2:18][CH2:19][CH2:20][N:8]3[C:7](=[O:21])[C:6]=2[CH:22]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]#[N:17])=[C:10]3[C@@H:9]3[CH2:18][CH2:19][CH2:20][N:8]3[C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 54277046HCID 54277046, compound

Product 1

HCID 53807155HCID 53807155, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6.31 g (21 mmol) of (S)-7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide were suspended in 20 ml of dioxan and 3.6 ml of pyridine and treated dropwise at 5° to 10° with 3.3 ml of trifluoroacetic anhydride. The reaction mixture was stirred at room temperature overnight and poured into 150 ml of water. The suspension obtained was filtered and the crystals were dried. There were obtained 5.36 g (90%) of (S)-7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile of m.p. 254°-256°.

Workup

  1. customThe suspension obtained
  2. filtrationwas filtered
  3. customthe crystals were dried

Sources & evidence

ORD record
ord-63460653439e43b7860c2c32627d105c
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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