Hydrochloric Acid → 2-[2-(5-Aminopyridin-3-yl)ethyl]-N(4)-(2-chloro-5-fluoropyrimidin-4-yl)benzene-1,4-diamine Trihydrochloride

HRID 541889Notes

Reaction equation

HRID 541889 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([F:22])=[CH:20][N:19]=[C:18]([Cl:23])[N:17]=2)=[CH:11][C:10]=1[CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([NH:32]C(=O)OC(C)(C)C)[CH:29]=[N:30][CH:31]=1)=O)(C)(C)C.CO.[ClH:42]>O1CCOCC1>[ClH:23].[ClH:42].[ClH:23].[NH2:32][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][C:10]2[CH:11]=[C:12]([NH:15][C:16]3[C:21]([F:22])=[CH:20][N:19]=[C:18]([Cl:23])[N:17]=3)[CH:13]=[CH:14][C:9]=2[NH2:8])[CH:31]=[N:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 57961769tert-Butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

Product 1

HCID 866362772-[2-(5-Aminopyridin-3-yl)ethyl]-N(4)-(2-chloro-5-fluoropyrimidin-4-yl)benzene-1,4-diamine TrihydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into the reaction flask was added tert-butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate (0.050 g, 0.089 mmol), methanol (0.6 mL), and 4.0 M of hydrogen chloride in 1,4-dioxane (1 mL). The mixture was stirred at rt overnight and concentrated under vacuum to give the desired product (10 mg, 95%). LCMS for C17H17ClFN6 (M+H)+: m/z=359.0.

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3844ed3820864d7ba61696074f0c7ea1
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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