Hydrochloric Acid → HCID 178525536, compound

HRID 2378692Notes

Reaction equation

HRID 2378692 reaction equation
[Br:1][C:2]1[C:10]2[C:9]3[CH2:11][N:12]([CH2:22][C:23]([F:26])([F:25])[F:24])[C:13](=[O:21])[C@H:14]([CH2:16][C:17]([O:19]C)=[O:18])[CH2:15][C:8]=3[CH:7]=[C:6]([Br:27])[C:5]=2[NH:4][N:3]=1.O.O.[OH-].[Li+].Cl>CO.O1CCCC1>[Br:1][C:2]1[C:10]2[C:9]3[CH2:11][N:12]([CH2:22][C:23]([F:24])([F:25])[F:26])[C:13](=[O:21])[C@H:14]([CH2:16][C:17]([OH:19])=[O:18])[CH2:15][C:8]=3[CH:7]=[C:6]([Br:27])[C:5]=2[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178500646(S)-Methyl 2-(1,4-dibromo-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetate

Product 1

HCID 178525536HCID 178525536, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(S)-Methyl 2-(1,4-dibromo-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetate (220 mg, 0.429 mmol) was dissolved in a mixture of methanol (5.0 mL) and tetrahydrofuran (5.0 mL). Water (5.0 mL) was added to the mixture followed by lithium hydroxide hydrate (66.0 mg, 1.573 mmol). Reaction was warmed to 60° C. and held with stirring for 1.25 hours. Mixture was cooled to room temperature and then neutralized with 1.6 mL 1N hydrochloric acid. Mixture was concentrated by roto-vap. Residue was partitioned between ethyl acetate and water. Layers were separated and the aqueous phase was discarded. Material was washed with brine and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 96% yield. MS (M−H)−=498.1, 496.1, 500.1.

Workup

  1. customReaction
  2. temperatureMixture was cooled to room temperature
  3. concentrationMixture was concentrated by roto-vap
  4. customResidue was partitioned between ethyl acetate and water
  5. customLayers were separated
  6. washMaterial was washed with brine
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a7862acba42a48f7afed549a5f220030
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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