Hydrochloric Acid → HCID 178428713, compound

HRID 505404Notes

Reaction equation

HRID 505404 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[N:17]=[C:16]([CH2:18][CH2:19][C:20]4[N:25]=[C:24]([NH2:26])[CH:23]=[C:22]([CH3:27])[CH:21]=4)[NH:15][C:12]3=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[ClH:29]>ClCCl.C(OCC)C>[ClH:29].[NH2:26][C:24]1[CH:23]=[C:22]([CH3:27])[CH:21]=[C:20]([CH2:19][CH2:18][C:16]2[NH:15][C:12]3=[N:13][CH:14]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([N:2]([CH3:28])[CH3:1])=[CH:4][CH:5]=4)[CH:10]=[C:11]3[N:17]=2)[N:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178428712HCID 178428712, compound

Product 1

HCID 178428713HCID 178428713, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

40 mg of 6-{2-[6-(4-dimethylamino-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine are dissolved in 8.0 ml of dichloromethane. After cooling the solution to 0° C., 53 μl of hydrochloride in diethyl ether (strength 2.0 M) is added under stirring. Subsequently, the solvents are evaporated in vacuo. The remaining residue is re-dissolved in 4 ml of dioxane containing 0.8 ml each of water and acetonitrile. The solution is lyophilized to yield 43 mg of the title compound. M.p. 142° C. (decomp.) TSP-MS: 373.3 (MH+). TLC: Rf=0.40 (dichloromethane/methanol 8:1).

Workup

  1. customSubsequently, the solvents are evaporated in vacuo
  2. dissolutionThe remaining residue is re-dissolved in 4 ml of dioxane containing 0.8 ml each of water and acetonitrile

Sources & evidence

ORD record
ord-0ee663abffd24be889b87040ca7af089
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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