Ammonia → [2-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazol-4-yl]-methylamine

HRID 473978Notes

Reaction equation

HRID 473978 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[S:10][C:11]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([CH3:23])[CH:17]=3)=[C:12](C#N)[N:13]=2)[CH2:3]1.[NH3:24].[H][H].[CH3:27]O>[Ni]>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[S:10][C:11]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([CH3:23])[CH:17]=3)=[C:12]([NH:24][CH3:27])[N:13]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 672165242-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazole-4-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 67216071[2-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazol-4-yl]-methylamine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Intermediate 4 (18.5 g, 56.33 mmol) was added to a suspension of Raney Nickel (2 g) in a 7 N ammonia solution in MeOH (250 mL). The reaction mixture was stirred at 14° C. under hydrogen atmosphere until 2 equivalents of hydrogen were absorbed. The catalyst was removed by filtration over diatomaceous earth. The solvent was evaporated, yielding Intermediate 5 quantitatively. Intermediate 5 was used without further purification.

Workup

  1. customwere absorbed
  2. customThe catalyst was removed by filtration over diatomaceous earth
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d5f056e9ed4842f5b3aa38078646076b
Source dataset
uspto-grants-2014_01
Patent number
US08637510B2

Reaction notes

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