Ammonia → HCID 13588037, compound

HRID 477661Notes

Reaction equation

HRID 477661 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=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].C[OH:32]>[Ni]>[OH2:32].[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:17]3[C:12]([N:11]=2)=[N:13][CH:14]=[CH:15][CH:16]=3)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 13588013HCID 13588013, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13588037HCID 13588037, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 12 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidineacetonitrile and 200 parts of methanol saturated with ammonia was hydrogenated at normal pressure and at room temperature with 2 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 acetonitrile, yielding 10 parts (78%) of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-imidazo[4,5-b]pyridin-2-amine monohydrate; mp. 116.9° C. (intermediate 109).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-527517f28c6f4c668cd9d5c1fb1268bb
Source dataset
uspto-grants-1989_12
Patent number
US04888426

Reaction notes

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