Water → HCID 58551415, compound

HRID 2204154Notes

Reaction equation

HRID 2204154 reaction equation
[F:1][C:2]1[C:7]2[N:8]3[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[C:9]3[C:10]3([CH2:16][CH2:15][N:14](C(=O)C(F)(F)F)[CH2:13][CH2:12]3)[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[F:1][C:2]1[C:7]2[N:8]3[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[C:9]3[C:10]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 58550744HCID 58550744, compound

Product 1

HCID 58551415HCID 58551415, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9′-fluoro-1-(2,2,2-trifluoroacetyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1′-carbonitrile (170 mg, 0.45 mmol) dissolved in MeOH (2.7 mL) was added K2CO3 (130 mg, 0.94 mmol) in one portion at rt. The reaction was monitored by LCMS until no starting material remained. Water was added (10 mL), and the organic solvent removed under vacuum. The product was extracted with dichloromethane (3×30 mL), the organic phases were combined, dried with sodium sulfate, filtered, concentrated to a white solid, which was used directly in next step without further purification (104 mg, 82%). ESI-MS m/z calc. 283.1, found 284.1 (M+1)+; Retention time 0.94 minutes (3 min run).

Workup

  1. customthe organic solvent removed under vacuum
  2. extractionThe product was extracted with dichloromethane (3×30 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid, which
  6. customwas used directly in next step without further purification (104 mg, 82%)
  7. customRetention time 0.94 minutes (3 min run)

Sources & evidence

ORD record
ord-8d8c3d947cb64ae89c3961cea3e556b8
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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