m-Chloroperbenzoic acid → 4-((8-((5-Cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide

HRID 1778109Notes

Reaction equation

HRID 1778109 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([C:14]1[C:15]([NH:44][CH2:45][CH2:46][O:47][CH3:48])=[CH:16][C:17]([NH:20][C:21]([N:23]2[C:32]3[C:27](=[CH:28][C:29]([CH2:35][N:36]4[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][C:37]4=[O:43])=[C:30]([CH:33]=[O:34])[N:31]=3)[CH2:26][CH2:25][CH2:24]2)=[O:22])=[N:18][CH:19]=1)#[N:13]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:12]([C:14]1[C:15]([NH:44][CH2:45][CH2:46][O:47][CH3:48])=[CH:16][C:17]([NH:20][C:21]([N:23]2[C:32]3[N:31]=[C:30]([CH:33]=[O:34])[C:29]([CH2:35][N:36]4[CH2:41][CH2:40][N+:39]([O-:6])([CH3:42])[CH2:38][C:37]4=[O:43])=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[O:22])=[N:18][CH:19]=1)#[N:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118036971Roblitinib

Product 1

HCID 1180368704-((8-((5-Cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoperoxoic acid (9.3 mg, 0.041 mmol) was added to a solution of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (Example 83, 20 mg, 0.039 mmol) in CHCl3 (0.1 ml) at 0° C. After stirring for 20 min, the mixture was warmed to room temperature and stirred for another 2 h. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3. The aqueous layer was back-extracted with DCM (2×). The combined organic layers were dried over Na2SO4 and evaporated. The residue was triturated with Et2O to give the title compound as a light purple solid.

Workup

  1. stirringstirred for another 2 h
  2. washwashed with sat. aq. NaHCO3
  3. extractionThe aqueous layer was back-extracted with DCM (2×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated
  6. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-5e25276cfa3d4100aa6936e3963840e3
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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