Ammonia → N-[1-(2-aminoethyl)-4-piperidinyl]-3-(2-pyridinylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine

HRID 620489Notes

Reaction equation

HRID 620489 reaction equation
Cl.FC1C=CC(CNC2C=NC=CC=2[N+]([O-])=O)=CC=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][N:27]1[C:31]2=[N:32][CH:33]=[CH:34][CH:35]=[C:30]2[N:29]=[C:28]1[NH:36][CH:37]1[CH2:42][CH2:41][N:40]([CH2:43][C:44]#[N:45])[CH2:39][CH2:38]1.N.[H][H]>[Ni].CO>[NH2:45][CH2:44][CH2:43][N:40]1[CH2:39][CH2:38][CH:37]([NH:36][C:28]2[N:27]([CH2:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)[C:31]3=[N:32][CH:33]=[CH:34][CH:35]=[C:30]3[N:29]=2)[CH2:42][CH2:41]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 135880184-[[3-(2-pyridinylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidineacetonitrileHCID 15614715HCID 15614715, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13588073N-[1-(2-aminoethyl)-4-piperidinyl]-3-(2-pyridinylmethyl)-3H-imidazo[4,5-b]pyridin-2-amineYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 17 parts of 4-[[3-(2-pyridinylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidineacetonitrile and 400 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 acetonitrile, yielding 15 parts (90%) of N-[1-(2-aminoethyl)-4-piperidinyl]-3-(2-pyridinylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine; mp. 151.1° C. (intermediate 102).

Workup

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

Sources & evidence

ORD record
ord-92a953fb7ac2483ba260481bd7e65ca5
Source dataset
uspto-grants-1989_04
Patent number
US04820822

Reaction notes

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