m-Chloroperbenzoic acid → HCID 68193665, compound

HRID 2370655Notes

Reaction equation

HRID 2370655 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14](SC)=[N:15][CH:16]=2)[N:11]2[CH:22]=[CH:23][N:24]=[C:10]12.ClC1C=C(C=CC=1)C(OO)=O.[NH2:36][C:37]1[CH:38]=[N:39][C:40]2[CH2:41][CH2:42][N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:44][C:45]=2[CH:46]=1>C(Cl)Cl.C(OCC)(=O)C>[C:50]([O:49][C:47]([N:43]1[CH2:42][CH2:41][C:40]2[N:39]=[CH:38][C:37]([NH:36][C:14]3[N:13]=[C:12]4[C:17]([C:18](=[O:19])[N:9]([C:3]5[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[C:10]5[N:11]4[CH:22]=[CH:23][N:24]=5)=[CH:16][N:15]=3)=[CH:46][C:45]=2[CH2:44]1)=[O:48])([CH3:53])([CH3:51])[CH3:52]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 11831817tert-Butyl 3-amino-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylateHCID 68194918HCID 68194918, compound

Product 1

HCID 68193665HCID 68193665, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 95C (70.0 mg, 0.193 mmol) and m-chloroperoxybenzoic acid (52.0 mg, 0.232 mmol) in CH2Cl2 (2 ml) was stirred for 20 minutes. tert-Butyl 3-amino-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (57.9 mg, 0.232 mmol) was added to the reaction mixture. After 5 hours, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous NaHCO3, and brine. The organic layer was dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with ethyl acetate to provide the title compound.

Workup

  1. washwashed with saturated aqueous NaHCO3, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on a 12 g column
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f498e491f5674e8ab2d67e65daebf958
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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