1,2-Diaminocyclohexane, cis- → HCID 58056218, compound

HRID 1773617Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20](Cl)[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(NC(C2C3N=C(O[N:47]4[C:51]5[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=5[N:49]=N4)N=CC=3SC=2)=O)C=CC=1OC.N[C@@H]1CCCC[C@@H]1N>O1CCOCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20]([NH:47][C@@H:51]4[CH2:52][CH2:53][CH2:54][CH2:55][C@@H:50]4[NH2:49])[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of the mixture of 85 mg of 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4-dimethoxy-phenyl)-amide and 2-(Benzotriazol-1-yloxy)-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4-dimethoxy-phenyl)-amide (from step a) and 0.17 g (1.41 mmole) of cis-1,2-diaminocyclohexane in Dioxane (3 mL) was stirred at 60° C. for overnight. The reaction were cooled down and diluted with CH2Cl2, washed with aqueous Na2CO3, brine, dried over anhydrous Na2SO4, concentrated and purified by flash chromatography (silica gel, 40 g, 0% to 30% MeOH (0.7 N) in CH2Cl2) to 50 mg of 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4-dimethoxy-phenyl)-amide as light yellow solid. MH+/Z=428.

Workup

temperatureThe reaction were cooled down
washwashed with aqueous Na2CO3, brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
custompurified by flash chromatography (silica gel, 40 g, 0% to 30% MeOH (0.7 N) in CH2Cl2) to 50 mg of 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4-dimethoxy-phenyl)-amide as light yellow solid

Sources & evidence

ORD record: ord-01ece9a778fc4344b5ef762c8e079a2a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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