Ammonia → HCID 13588034, compound

HRID 280333Notes

Reaction equation

HRID 280333 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]#[N:27])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.N.[H][H]>[Ni].CO>[NH2:27][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][CH:19]([NH:18][C:10]2[N:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 13588011HCID 13588011, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13588034HCID 13588034, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 15 parts of 4-[[3-[(4-fluorophenyl)methyl]-3H-imidazo [4,5-b]pyridin-2-yl]amino]-1-piperidineacetonitrile and 400 15 parts of methanol saturated with ammonia was hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybis-propane, yielding 10 parts (68%) of N-[1-(2-aminoethyl)-4-piperidinyl]-3-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine; mp. 174.5° C. (50). In a similar manner there were also prepared:

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybis-propane

Sources & evidence

ORD record
ord-e4d0b0b612c3406885ba016fb93ed4ad
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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