Pyrazole → HCID 11642199, compound

HRID 556420Notes

Reaction equation

HRID 556420 reaction equation
[CH2:1]([O:3][C:4]1[C:5]2[S:18][C:17]3[N:19]=[C:20]([C:27]4[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=4)[CH:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[C:16]=3[C:6]=2[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:9]=1)[CH3:2].[NH:34]1[CH:38]=[CH:37][CH:36]=[N:35]1.CN[C@@H]1CCCC[C@H]1NC>CN(C)C=O.[Cu]I>[CH2:1]([O:3][C:4]1[C:5]2[S:18][C:17]3[N:19]=[C:20]([C:27]4[CH:32]=[CH:31][C:30]([N:34]5[CH:38]=[CH:37][CH:36]=[N:35]5)=[CH:29][CH:28]=4)[CH:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[C:16]=3[C:6]=2[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 11497962HCID 11497962, compound

Product 1

HCID 11642199HCID 11642199, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

0.30 g (0.5 mmol) 4-ethoxy-9-trifluoromethyl-7-(4-iodo-phenyl)-2-piperazin-1-yl-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine, 0.14 g (2.1 mmol) pyrazole, 0.22 g (1.0 mmol) potassiumphosphate-tribasic, 0.06 g (0.3 mmol) copper(I)-iodide and 0.014 g (0.1 mmol) (1R,2R)—N,N′-dimethyl-1,2-cyclohexanediamine in 5 ml N,N-dimethylformamide (dry) are stirred at 110° C. under nitrogen atmosphere for 24 h. The solvent is removed in vacuo and the residue is suspended in 20 ml water, sucked off, washed with 100 ml water and suck dried. Following purification by means of flash chromatography (methanol/dichloromethane 1:10) 0.04 g (15%) 4-ethoxy-9-trifluoromethyl-2-piperazin-1-yl-7-(4-(1H-pyrazol-1-yl)-phenyl)-pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidine is obtained.

Workup

  1. customThe solvent is removed in vacuo
  2. washwashed with 100 ml water and suck
  3. customdried
  4. custompurification by means of flash chromatography (methanol/dichloromethane 1:10) 0.04 g (15%) 4-ethoxy-9-trifluoromethyl-2-piperazin-1-yl-7-(4-(1H-pyrazol-1-yl)-phenyl)-pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidine
  5. customis obtained

Sources & evidence

ORD record
ord-47b399679a8c4a0aa3cbb7370fad7f95
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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