Potassium Hydroxide → HCID 68358955, compound

HRID 1408970Notes

Reaction equation

HRID 1408970 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11]([NH:12][C@@H:13]3[CH2:17][CH2:16][C@:15]([CH3:22])([C:18]([O:20]C)=[O:19])[C:14]3([CH3:24])[CH3:23])=[C:10]([C:25](=[O:27])[NH2:26])[CH:9]=[N:8][N:7]2[CH:28]=1>C(O)C.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:11]([NH:12][C@@H:13]3[CH2:17][CH2:16][C@:15]([CH3:22])([C:18]([OH:20])=[O:19])[C:14]3([CH3:24])[CH3:23])=[C:10]([C:25](=[O:27])[NH2:26])[CH:9]=[N:8][N:7]2[CH:28]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68358957HCID 68358957, compound

Product 1

HCID 68358955HCID 68358955, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A 4.5 M aqueous solution of potassium hydroxide (210 μl, 0.945 mmol) was added dropwise to a solution of (1S,3R)-methyl 3-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-1,2,2-trimethylcyclopentanecarboxylate (200 mg, 0.472 mmol) in ethanol (3.2 ml). The reaction was heated at 75° C. for 24 hrs. The reaction was cooled to room temperature and concentrated under reduced pressure to yield an oil. The oil was diluted with ethyl acetate and washed with water. The aqueous layer was acidified with 1.0 N HCl and was extracted with ethyl acetate (3×). The organic extracts were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure, yielding the title compound (182 mg, 0.422 mmol, 89% yield) as a pale yellow solid. LC/MS found [M+H]+=410.7.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto yield an oil
  4. washwashed with water
  5. extractionwas extracted with ethyl acetate (3×)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93e3448b05cd4a2baf30bc8a075e6c91
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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