Water → HCID 86660254, compound

HRID 2204088Notes

Reaction equation

HRID 2204088 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:23]([CH:24]=[O:25])=[CH:22][CH:21]=[C:7]3[C:8]3([CH2:14][CH2:13][N:12](C(=O)C(F)(F)F)[CH2:11][CH2:10]3)[O:9][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:23]([CH:24]=[O:25])=[CH:22][CH:21]=[C:7]3[C:8]3([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86660253HCID 86660253, compound

Product 1

HCID 86660254HCID 86660254, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 7′-chloro-1-(2,2,2-trifluoroacetyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1′-carbaldehyde (510 mg, 1.28 mmol) dissolved in MeOH (5.1 mL) was added K2CO3 (371 mg, 2.69 mmol) in one portion at room temperature. Water was added (2 mL), and organic solvent was removed under vacuum. The mixture was extracted with DCM (3×10 mL). The organics were combined, dried, filtered, and concentrated to give 7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbaldehyde as a yellow oil, which was used as is for the following step. ESI-MS m/z calc. 302.1, found 303.3 (M+1)+; Retention time: 1.07 minutes (3 min run).

Workup

  1. customwas removed under vacuum
  2. extractionThe mixture was extracted with DCM (3×10 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db87b7eb352b471284a525acae8e8d06
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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