Hydrochloric Acid → HCID 68155983, compound

HRID 1877794Notes

Reaction equation

HRID 1877794 reaction equation
[Sn](Cl)Cl.Cl.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([N+:27]([O-])=O)=[C:10]([CH:26]=1)[CH2:11][N:12]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]1[C:21](OCC)=[O:22]>C(O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:27][C:21](=[O:22])[C:13]3=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][N:12]3[CH2:11][C:10]=2[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 68155864HCID 68155864, compound

Product 1

HCID 68155983HCID 68155983, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add tin dichloride (3 equiv; 3.02 g, 15.77 mmol) in 5M hydrochloric acid (20 mL, 100 mmol) to ethyl 1-(5-chloro-2-nitrobenzyl)-4-(trifluoromethyl)-1H-pyrrole-2-carboxylate (1 equiv; 1.98 g, 5.26 mmoles) and ethanol (100 mL) at 50° C. Heat overnight and then for a further 26 h, remove most of the ethanol in vacuo and dilute the resultant solution with water and collect the resultant precipitate by filtration, wash well with water and dry in vacuo at 40° C. Absorb the solid onto silica, chromatograph eluting with DCM/methanol (5:95) to give uncyclised amino ester (0.260 g) and 7-chloro-2-(trifluoromethyl)-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one (0.613 g). Heat the uncyclised ester in a mixture of 5M hydrochloric acid (10 mL, 50 mmol) for 80 h. Remove the ethanol in vacuo and collect the resultant precipitated solid by filtration and wash with water to give 7-chloro-2-(trifluoromethyl)-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one (0.17 g). Combine with earlier 7-chloro-2-(trifluoromethyl)-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one to give (0.794 g, 50% yield). MS (m/z): 300.99 (M+1).

Workup

  1. temperatureHeat overnight
  2. customremove most of the ethanol in vacuo
  3. additiondilute the resultant solution with water
  4. customcollect the resultant precipitate
  5. filtrationby filtration
  6. washwash well with water
  7. customdry in vacuo at 40° C
  8. customAbsorb the solid onto silica, chromatograph
  9. washeluting with DCM/methanol (5:95)

Sources & evidence

ORD record
ord-1db7797c0e2049a7bc81684f8e0a6f41
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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