HCID 178504840, compound → HCID 178511655, compound

HRID 1634059Notes

Reaction equation

HRID 1634059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:21]([OH:22])=[N:20][C:11]2[N:12]=[C:13](S(C)(=O)=O)[N:14]=[CH:15][C:10]=2[CH:9]=1.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>CN1CCCC1=O.C(OCC)(=O)C>[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([NH:30][C:13]2[N:14]=[CH:15][C:10]3[CH:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:21]([OH:22])=[N:20][C:11]=3[N:12]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 178504840HCID 178504840, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511655HCID 178511655, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of sulfone 2 (1.27 g, 3.78 mmol) in 15 mL of 1-methyl-2-pyrrolidinone was added trans-1,4-diaminocyclohexane (3.75 g, 32.8 mmol). The reaction mixture was stirred at 65° C. for 1.5 hours, cooled, and diluted with 80 mL of ethyl acetate. The resulting suspension was filtered and washed several times with ethyl acetate and methanol. The solid was dried to yield 1.31 g (94%) of 2-(trans-4-aminocyclohexylamino)-6-(2-chlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol as an off-white powder (mass spec. M+H+=370). The free base was taken up in ethyl acetate and treated with a 1M solution of HCl/Et2O to form the dihydrochloride salt of the title compound as a white powder with a melting point of >300° C.

Workup

  1. temperaturecooled
  2. filtrationThe resulting suspension was filtered
  3. washwashed several times with ethyl acetate and methanol
  4. customThe solid was dried

Sources & evidence

ORD record
ord-4e72912ad6b74a788c5a19470c437f92
Source dataset
uspto-grants-2003_01
Patent number
US06506749B2

Reaction notes

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