Acetone → 1-(1-Methylethyl)-4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane

HRID 1402757Notes

Reaction equation

HRID 1402757 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:13][CH:12]([C:14]([N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:23][C:24]([CH3:26])=O>CCO.[Pd]>[CH3:23][CH:24]([N:19]1[CH2:20][CH2:21][CH2:22][N:16]([C:14]([CH:12]2[CH2:13][N:10]([C:8]([C:5]3[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[O:9])[CH2:11]2)=[O:15])[CH2:17][CH2:18]1)[CH3:26]

Participants

5

Reactant 2

HCID 180AcetoneHCID 667401031-({1-[(6-Methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane

Product 1

HCID 468529061-(1-Methylethyl)-4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepaneYield 27.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 1-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane (60 mg, 0.194 mmol) in EtOH (3 mL) was added Pd/C (10% wt/wt, 6 mg) and acetone (143 μL, 1.95 mmol). The flask was purged with N2 (N2/vacuum cycle×3) and then H2 (H2/vacuum cycle×3). After 24 hours the reaction was filtered through Celite® and concentrated at reduced pressure. Purification by silica FCC (90:9:1 Et2O/MeOH/NH3) and capture and release (SCX-2, flush with MeOH, then release with 7M NH3 in MeOH) gave the title compound (18.4 mg, 27%).

Workup

  1. customThe flask was purged with N2 (N2/vacuum cycle×3)
  2. filtrationAfter 24 hours the reaction was filtered through Celite®
  3. concentrationconcentrated at reduced pressure
  4. customPurification by silica FCC (90:9:1 Et2O/MeOH/NH3) and capture and release (SCX-2,
  5. customflush with MeOH

Sources & evidence

ORD record
ord-5783bbe9b4d84a0f9c7288b53dbf6e3a
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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