Potassium Hydroxide → HCID 68358882, compound

HRID 1408968Notes

Reaction equation

HRID 1408968 reaction equation
[OH-].[K+].[C:3]([C:6]1[CH:11]=[N:10][N:9]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=[C:8]2[C:7]=1[NH:21][C@@H:22]1[CH2:26][CH2:25][C@:24]([CH3:31])([C:27]([O:29]C)=[O:28])[C:23]1([CH3:33])[CH3:32])(=[O:5])[NH2:4]>C(O)C.C(OCC)(=O)C>[C:3]([C:6]1[CH:11]=[N:10][N:9]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=[C:8]2[C:7]=1[NH:21][C@@H:22]1[CH2:26][CH2:25][C@:24]([CH3:31])([C:27]([OH:29])=[O:28])[C:23]1([CH3:33])[CH3:32])(=[O:5])[NH2:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68291057HCID 68291057, compound

Product 1

HCID 68358882HCID 68358882, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A 4.5 M aqueous potassium hydroxide (192 μl, 0.866 mmol) solution was added dropwise to a solution of (1S,3R)-methyl 3-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)-1,2,2-trimethyl-cyclopentanecarboxylate (182 mg, 0.433 mmol) in ethanol (2885 μl). The reaction was heated at 75° C. for 24 hrs. The reaction was cooled to room temperature and concentrated under reduced pressure, yielding 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 (1S,3R)-3-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)-1,2,2-trimethylcyclopentanecarboxylic acid (152.8 mg, 0.376 mmol, 87% yield) as a yellow solid. LC/MS found [M+H]+=407.0.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customyielding 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-64ac38e95e7b40b3807c914abf3f419b
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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