Morpholine → HCID 117667432, compound

HRID 1526265Notes

Reaction equation

HRID 1526265 reaction equation
[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:36]=[CH:37][CH:38]=1)[O:9][C:10]1[N:11]=[C:12]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]3)=[C:24]([CH3:35])[CH:23]=2)[C:13]([C:18]([NH2:20])=[O:19])=[N:14][C:15]=1[CH2:16][CH3:17])(=[O:4])[CH:2]=[CH2:3].[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O.ClCCCl>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:36]=[CH:37][CH:38]=1)[O:9][C:10]1[N:11]=[C:12]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][CH:31]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH2:30][CH2:29]3)=[C:24]([CH3:35])[CH:23]=2)[C:13]([C:18]([NH2:20])=[O:19])=[N:14][C:15]=1[CH2:16][CH3:17])(=[O:4])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 117667408HCID 117667408, compound

Product 1

HCID 117667432HCID 117667432, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a mixture of 5-[3-(acryloylamino)phenoxy]-6-ethyl-3-{[3-methyl-4-(4-oxopiperidin-1-yl)phenyl]amino}pyrazine-2-carboxamide (200 mg), morpholine (35 μL), and 1,2-dichloroethane (1.94 mL) was added sodium triacetoxyborohydride (100 mg), followed by stirring at room temperature overnight. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and water, followed by extraction with chloroform twice. The extract was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0-99:1-97:3) to obtain 5-[3-(acryloylamino)phenoxy]-6-ethyl-3-({3-methyl-4-[4-(morpholin-4-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (55 mg) as a solid.

Workup

  1. extractionfollowed by extraction with chloroform twice
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0-99:1-97:3)

Sources & evidence

ORD record
ord-4075d53df26e417a82024534950b15ca
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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