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2-Amino-5-chloropyridine → N-(5-chloropyridin-2-yl)-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzamide

HRID 1373712
Notes
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Reaction equation

HRID 1373712 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C[Mg]Br.[O:12]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]3[O:27][C:26](=[O:28])[C:25]4[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=4[N:23]=3)[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1>O1CCCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:26](=[O:28])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[NH:23][C:22]([N:19]2[CH2:18][CH2:17][C:16]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:21][CH2:20]2)=[O:27])=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 661742-Amino-5-chloropyridineHCID 219066372-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)-4H-3,1-benzoxazin-4-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 21906181N-(5-chloropyridin-2-yl)-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzamide

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-amino-5-chloropyridine (573 mg, 4.51 mmol) in tetrahydrofuran (25 mL) at 0° C. under nitrogen was added methylmagnesium bromide (3.0 M in ether, 1.50 mL, 4.51 mmol) dropwise via a syringe. After stirring at 0° C. for 10 min, 2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4H-3,1-benzoxazin-4-one (1.30 g, 4.51 mmol) was added. After stirring 15 h at room temperature, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and saturated aqueous sodium chloride and the layers separated. The organic phase was washed with water, dried (magnesium sulfate), filtered, and concentrated in vacuo to give, after recrystallization from EtOAc, 880 mg (47%) of the title compound.

Workup

  1. stirringAfter stirring 15 h at room temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium chloride
  4. customthe layers separated
  5. washThe organic phase was washed with water
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give
  10. customafter recrystallization from EtOAc, 880 mg (47%) of the title compound

Sources & evidence

ORD record
ord-85b31b7d1c844ff081e6584a3b9c7753
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07163938B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes