Acetone → HCID 131730965, compound

HRID 2035503Notes

Reaction equation

HRID 2035503 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:20]=[CH:19][C:18]([CH2:21][C:22]([NH2:24])=[O:23])=[C:17]([NH:25][CH2:26][C:27]4[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=4)[CH:16]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:35][C:36]([CH3:38])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O.C(O)(=O)C>[F:33][C:31]1[CH:32]=[C:27]([CH:28]=[C:29]([F:34])[CH:30]=1)[CH2:26][NH:25][C:17]1[CH:16]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([N:1]3[CH2:7][CH2:6][CH2:5][N:4]([CH:36]([CH3:38])[CH3:35])[CH2:3][CH2:2]3)=[CH:9][CH:10]=2)[N:20]=[CH:19][C:18]=1[CH2:21][C:22]([NH2:24])=[O:23]

Participants

8

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 131730966HCID 131730966, compound

Product 1

HCID 131730965HCID 131730965, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

60 mg of 6-{[4-(1,4-diazepan-1-yl)phenyl]amino}-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 227) was suspended in 1.5 mL of chloroform, to which 0.2 mL of acetone, 4.1 mg of acetic acid and 58 mg of sodium triacetoxyborohydride were added, and stirred at room temperature for 4 hours. To the reaction mixture, saturated sodium bicarbonate in water was added, extracted with chloroform, and the extract was dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=20:1), recrystallized from methanol-ether to obtain 37 mg (53%) of the title compound as a white crystalline powder.

Workup

  1. additionwere added
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=20:1)
  6. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-c052f7e8b2b84098a74223829445df7f
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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