Water → HCID 86660254, compound

HRID 1908002Notes

Reaction equation

HRID 1908002 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-54ec4cd3b0f548339a78b9e4026108d4
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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