Ammonium Hydroxide → HCID 67070155, compound

HRID 2390849Notes

Reaction equation

HRID 2390849 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)([C:11]#[N:12])[CH3:10])[CH:7]=1.[NH4+].[OH-]>CO.[Ni]>[NH2:12][CH2:11][C:9]([C:13]1[CH:14]=[CH:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:17][CH:18]=1)([CH3:10])[CH2:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([C:26]([CH3:28])([CH3:29])[CH3:27])[C:5]=1[O:24][CH3:25]

Participants

5

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 67070089HCID 67070089, compound

Product 1

HCID 67070155HCID 67070155, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 887MethanolSolvent

Procedure

step 1—To a solution of 288 (150 mg, 0.313 mmol) in MeOH (20 mL) in a Parr bottle was added Raney Nickel (50% solution in water, 1 mL) and NH4OH (0.5 mL) and the mixture was hydrogenated at 45 psi on a Parr shaker overnight. LCMS indicated some remaining starting material. Additional Raney Nickel (1 mL) and NH4OH (0.5 mL) were added and the hydrogenation was continued for another day. The crude mixture was filtered through CELITE and the filtrate was concentrated. The crude product was purified by SiO2 chromatography eluting with 10% MeOH/DCM to afford 127 mg (84%) of N-{4-[1-aminomethyl-2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-1-methyl-ethyl]-phenyl}-methanesulfonamide (290).

Workup

  1. customwas hydrogenated at 45 psi on a Parr shaker overnight
  2. waitthe hydrogenation was continued for another day
  3. filtrationThe crude mixture was filtered through CELITE
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-697864f0f3604c48a6472389e03e3749
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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