Acetic Acid → HCID 67468393, compound

HRID 2204084Notes

Reaction equation

HRID 2204084 reaction equation
[CH:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[C:7]3([CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[CH2:15][CH2:14]3)[O:6][C:5]=2[N:4]=[CH:3][CH:2]=1.CC(O)=O>CO.[Pd]>[CH:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[C:7]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:6][C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 58551020HCID 58551020, compound

Product 1

HCID 67468393HCID 67468393, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate (220 mg, 0.586 mmol), AcOH (33 μL, 0.59 mmol) and Pd/C (22 mg, 0.21 mmol) in MeOH (2 mL) was stirred under a balloon on H2 for 6 hours. The mixture was filtered through celite and the filtrate was evaporated to give spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine] (ESI-MS m/z calc. 241.1, found 242.5 (M+1)+; Retention time: 0.46 minutes (3 min run)). The residue was then taken up in THF (3 mL) before Na2CO3 (1.2 mL of 2.0 M, 2.4 mmol) was added. Boc2O (156 mg, 0.70 mmol) was added and the mixture was stirred at room temperature for 12 hours. N,N-dimethylethylenediamine (0.5 mL) was added and the mixture was stirred at room temperature for 30 min. The mixture was poured into water and was extracted with EtOAc (3×). The organics were combined, washed with 0.1N HCl (3×), brine, dried (Na2SO4) and filtered through a plug of silica to give tert-butyl spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate (134 mg, 67%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9e6b0afde9174ff38c776eefd48341ed
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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