Hydrochloric Acid → 9-(1-Isopropyl-1H-pyrazol-5-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylic acid

HRID 1799837Notes

Reaction equation

HRID 1799837 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[CH2:17][CH2:16][O:15][C:14]4[CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[CH:20]=[N:21][C:13]=4[N:12]3[CH:26]=2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[Li+].[OH-].Cl>CO.O1CCCC1>[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[CH2:17][CH2:16][O:15][C:14]4[CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=[N:21][C:13]=4[N:12]3[CH:26]=2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58204755Methyl 9-(1-isopropyl-1H-pyrazol-5-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylate

Product 1

HCID 582043789-(1-Isopropyl-1H-pyrazol-5-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 21 mg (0.06 mmol) of methyl 9-(1-isopropyl-1H-pyrazol-5-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylate and 1.0 ml of 1 N aq LiOH in 4 ml of methanol and 4 ml of tetrahydrofuran was stirred for 6 hours. The mixture was acidified to pH 3 by addition of 1 N HCl and concentrated in vacuum. The residue was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried over Na2SO4 and concentrated. Yield 17 mg. MS (ESI+): 340.1

Workup

  1. concentrationconcentrated in vacuum
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-956c7cd43d3f44b3adbf89536bf0eb24
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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