Hydrochloric Acid → HCID 86626131, compound

HRID 2080296Notes

Reaction equation

HRID 2080296 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][CH:40]=1)[CH2:5][CH2:6][NH:7][C:8]1[N:32]=[C:31]([C:33]2[CH:34]=[N:35][NH:36][CH:37]=2)[CH:30]=[CH:29][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[C:15]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:11].Cl>CO.O1CCOCC1>[CH3:10][OH:11].[NH2:21][CH2:20][C:15]1[C:14]([CH2:13][NH:12][C:10](=[O:11])[C:9]2[CH:29]=[CH:30][C:31]([C:33]3[CH:34]=[N:35][NH:36][CH:37]=3)=[N:32][C:8]=2[NH:7][CH2:6][CH2:5][C:4]2[CH:38]=[CH:39][CH:40]=[C:2]([F:1])[CH:3]=2)=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57542802HCID 57542802, compound

Product 1

HCID 86626131HCID 86626131, compoundYield 179.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (3-((2-(3-fluorophenethylamino)-6-(1H-pyrazol-4-yl)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)-2-(3-fluorophenethylamino)-6-(1H-pyrazol-4-yl)nicotinamide compound with methanol (1:1) as a pale yellow solid (545 mg, 89%). LRMS (M+H+) m/z 446.2.

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-9f553100a1a34a11aa9fdab156958769
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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