Hydrochloric Acid → N-((2-(aminomethyl)pyridin-3-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide

HRID 2080282Notes

Reaction equation

HRID 2080282 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:33]=[CH:32][C:12]([C:13]([NH:15][CH2:16][C:17]2[C:18]([CH2:23][NH:24]C(=O)OC(C)(C)C)=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[C:11]([NH:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)[N:10]=1)#[N:2].Cl>CO.O1CCOCC1>[NH2:24][CH2:23][C:18]1[C:17]([CH2:16][NH:15][C:13](=[O:14])[C:12]2[CH:32]=[CH:33][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])=[N:10][C:11]=2[NH:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=2)=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57542397Tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate

Product 1

HCID 57542571N-((2-(aminomethyl)pyridin-3-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate (737 mg, 1.27 mmol) in methanol (6 mL) at 0° C. was added a solution of 4M HCl in 1,4-dioxane (3 mL). The mixture was warmed to room temperature and stirred for 2 hrs. Concentration of the mixture followed by the purification on RP-HPLC using a mixture of acetonitrile and H2O gave N-((2-(aminomethyl)pyridin-3-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide as a pale yellow solid (545 mg, 89%). LRMS (M+H+) m/z 481.2.

Workup

  1. customConcentration of the mixture followed by the purification on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-55395a3fd81f40de89e3e2997cb10cae
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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