Water → HCID 131723670, compound

HRID 31784Notes

Reaction equation

FC(S(O[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[N:12]=[C:11]([NH:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[N:10]=1)(=O)=O)(F)F.O.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C(#N)C>[C:30]([O:29][C:27]([NH:26][CH2:25][CH2:24][NH:23][C:11]1[N:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH:14]=[C:9]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[N:10]=1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 90 °C

Procedure

2-({2-[(tert-butoxy)carbonylamino]ethyl}amino)-6-(4-cyanophenyl)pyrimidin-4-yl (trifluoromethyl)sulfonate (134 mg, 0.275 mmol) was dissolved in a 2 M solution of morpholine in acetonitrile and the resulting solution heated to 90° C. for 18 h. The solution was cooled, water added and the suspension extracted thoroughly with ethyl acetate. Concentration of the combined organic layers gave a crude solid which was chromatographed (silica gel, 2% methanol/methylene chloride) to afford 234 mg of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-6-morpholin-4-ylpyrimidin-2-yl]amino}ethyl)-carboxamide as a off white solid. Removal of the tert-butoxy protecting group was accomplished in the following manner: the (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-6-morpholin-4-ylpyrimidin-2-yl]amino}ethyl)carboxamide produced as described above was dissolved in anhydrous hydrogen chloride in dioxane (2 mL of a 2M solution) and stirred at room temperature for 2 h. Concentration gave 134 mg of 4-{2-[(2-aminoethyl)amino]-6-imidazolyl-4-ylpyrimidin-4-yl}benzenecarbonitrile as its (2×) hydrochloride salt.

Workup

temperatureThe solution was cooled
extractionthe suspension extracted thoroughly with ethyl acetate
customConcentration of the combined organic layers gave a crude solid which
customwas chromatographed (silica gel, 2% methanol/methylene chloride)

Sources & evidence

ORD record: ord-0e879e700da4442da37a86e236da18b7
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425557B2

Reaction notes

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