HCID 58495512, compound → HCID 28755594, compound

HRID 1191032Notes

Reaction equation

HRID 1191032 reaction equation
[CH3:1][N:2]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1>C1COCC1.C(O)(C)C.[Pd]>[CH3:1][N:2]([C:11](=[O:16])[C:12]([CH3:14])([CH3:13])[CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH2:8])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 58495512HCID 58495512, compound

Product 1

HCID 28755594HCID 28755594, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

Add a solution of 4-(N-methyl-2,2-dimethyl-propionylamino)-benzonitrile (55 mg, 0.25 mmol) in THF/iso-propanol (1:1, 8 mL) to 10% Pd/C (Degussa type E101, 31 mg, 0.15 mmol) under nitrogen. Purge the reaction mixture with nitrogen and then submit to hydrogenation at 50 psi for 1 h. Filter the catalyst through Celite® and wash thoroughly with THF (100 mL) and iso-propanol (100 mL). Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with DCM/2M ammonia in methanol (1:0 to 9:1 gradient over 30 min and 9:1 over 3 min; 35 mL/min) to obtain the title compound as a colorless oil (41 mg, 73%). MS (ES+) m/z: 221.2 (M+H)+.

Workup

  1. customPurge the reaction mixture with nitrogen
  2. filtrationFilter the catalyst through Celite®
  3. washwash thoroughly with THF (100 mL) and iso-propanol (100 mL)
  4. concentrationConcentrate in vacuo
  5. custompurify the crude mixture by chromatography on silica gel eluting with DCM/2M ammonia in methanol (1:0 to 9:1 gradient over 30 min and 9:1 over 3 min; 35 mL/min)

Sources & evidence

ORD record
ord-cf939e7899b64080a814162880ad168d
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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