1,2-Diaminocyclohexane, cis- → HCID 56646341, compound

HRID 1773616Notes

Reaction equation

HRID 1773616 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([C:13]3[C:17]4[N:18]=[C:19](Cl)[N:20]=[CH:21][C:16]=4[S:15][CH:14]=3)=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.O1C2C=CC(NC(C3C4N=C(O[N:45]5[C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=6[N:47]=N5)N=CC=4SC=3)=O)=CC=2OC1.N[C@@H]1CCCC[C@@H]1N>O1CCOCC1.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([C:13]3[C:17]4[N:18]=[C:19]([NH:45][C@@H:49]5[CH2:50][CH2:51][CH2:52][CH2:53][C@@H:48]5[NH2:47])[N:20]=[CH:21][C:16]=4[S:15][CH:14]=3)=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 3429171,2-Diaminocyclohexane, cis-HCID 66664866HCID 66664866, compoundHCID 86661376HCID 86661376, compound

Product 1

HCID 56646341HCID 56646341, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of the mixture of 80 mg of 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid benzo[1,3]dioxol-5-ylamide and 2-(Benzotriazol-1-yloxy)-thieno[3,2-d]pyrimidine-7-carboxylic acid benzo[1,3]dioxol-5-ylamide (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 40 mg of 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid benzo[1,3]dioxol-5-ylamide as light yellow solid. MH+/Z=412.

Workup

  1. temperatureThe reaction were cooled down
  2. washwashed with aqueous Na2CO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel, 40 g, 0% to 30% MeOH (0.7 N) in CH2Cl2) to 40 mg of 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid benzo[1,3]dioxol-5-ylamide as light yellow solid

Sources & evidence

ORD record
ord-fbb3b9215f804c0f8d51aec260dc161b
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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