Water → HCID 131730977, compound

HRID 2035513Notes

Reaction equation

HRID 2035513 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[C:11]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:10]=2)=[CH:4][CH:3]=1.[C:27]([N:34]1[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1(C)C=CC=CC=1.O1CCCC1>[CH2:20]([NH:19][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH:37]3[CH2:38][CH2:39][N:34]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:35][CH2:36]3)=[CH:7][CH:6]=2)[N:14]=[CH:13][C:12]=1[CH2:15][C:16]([NH2:18])=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 131730943HCID 131730943, compound

Product 1

HCID 131730977HCID 131730977, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

30 mg of 6-[(4-aminophenyl)amino]-4-(benzylamino) pyridine-3-carboxyamide (Example 65) was dissolved in 2 mL of toluene and 2 mL of tetrahydrofuran, to which 54 mg of 1-Boc-4-piperidone and 38 mg of sodium triacetoxyborohydride were added, and stirred at room temperature for 19 hours. To the reaction mixture, water was added, extracted with chloroform, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1) to obtain 28 mg (60%) of the title compound as a light brown crystalline powder.

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-83f6f20a936d4d01a15e7918d8bee02e
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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