Hydrochloric Acid → HCID 67467254, compound

HRID 1908048Notes

Reaction equation

HRID 1908048 reaction equation
C(O[CH:4](OCC)[CH:5]1[C:14]2([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[O:13][C:12]2[C:7](=[CH:8][C:9]([F:27])=[CH:10][CH:11]=2)[C:6]1=O)C.[ClH:32].[CH3:33][NH:34][NH2:35]>>[ClH:32].[F:27][C:9]1[CH:10]=[CH:11][C:12]2[O:13][C:14]3([C:5]4[C:6](=[N:35][N:34]([CH3:33])[CH:4]=4)[C:7]=2[CH:8]=1)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 58550804HCID 58550804, compound

Product 1

HCID 67467254HCID 67467254, compoundYield 29.6%

Procedure

To tert-butyl 3-(diethoxymethyl)-6-fluoro-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylate (3.81 g, 8.71 mmol) was added hydrochloric acid (32.7 mL of 4.0 M in dioxane, 130 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under vacuum, and the obtained solid was azeotroped with EtOH (1×30 mL). The resulting solid was suspended in EtOH (30.5 mL) and was treated with methylhydrazine (556 μL, 10.5 mmol) at 40° C. for 4 h. The mixture was then heated at 80° C. for 1 h resulting in a yellow solution with an off white precipitate. The solid was collected to give 8-fluoro-2-methyl-2H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]hydrochloride (798 mg, 26%). ESI-MS m/z calc. 273.1. found 274.5 (M+1)+. Retention time 0.83 minutes (3 min run). Note: The yellow mother liquor was evaporated to give a mixture of methyl regioisomers (1.71 g).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe obtained solid was azeotroped with EtOH (1×30 mL)
  3. temperatureThe mixture was then heated at 80° C. for 1 h
  4. customresulting in a yellow solution with an off white precipitate
  5. customThe solid was collected

Sources & evidence

ORD record
ord-18c9c0d81aab42418e5266b269f28d19
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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