1,2-Diaminocyclohexane, cis- → HCID 58056174, compound

HRID 1773615Notes

Reaction equation

HRID 1773615 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[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:4]=[CH:3][CH:2]=1.[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[NH:34]C(C2C3N=C(ON4C5C=CC=CC=5N=N4)N=CC=3SC=2)=O)C=CC=1.N[C@@H]1CCCC[C@@H]1N>O1CCOCC1.C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20]([NH:24][C@@H:33]4[CH2:28][CH2:29][CH2:30][CH2:31][C@@H:32]4[NH2:34])[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 3429171,2-Diaminocyclohexane, cis-HCID 66664602HCID 66664602, compoundHCID 86661375HCID 86661375, compound

Product 1

HCID 58056174HCID 58056174, 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 quinolin-8-ylamide and 2-(benzotriazol-1-yloxy)-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-8-ylamide and 0.17 g (1.41 mmole) of cis-1,2-diaminocyclohexane (from step a) 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 quinolin-8-ylamide as light yellow solid. MH+/Z=419.

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 quinolin-8-ylamide as light yellow solid

Sources & evidence

ORD record
ord-abbb5d93fbc54c998a50fba17e451ca4
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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