1,1'-Carbonyldiimidazole → N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-N'-[2-(methylsulfonyl)ethyl]urea

HRID 1926086Notes

Reaction equation

HRID 1926086 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)=[C:18]([Cl:33])[CH:17]=3)=[N:12][CH:11]=[N:10][C:9]=2[CH:8]=[CH:7]1.[C:34](N1C=CN=C1)([N:36]1[CH:40]=[CH:39]N=C1)=[O:35].[CH3:46][S:47](CCN)(=[O:49])=[O:48].C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[Cl:33][C:18]1[CH:17]=[C:16]([NH:15][C:13]2[C:14]3[N:6]([CH2:5][CH2:4][NH:3][C:34]([NH:36][CH2:40][CH2:39][S:47]([CH3:46])(=[O:49])=[O:48])=[O:35])[CH:7]=[CH:8][C:9]=3[N:10]=[CH:11][N:12]=2)[CH:21]=[CH:20][C:19]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 43405612-(Methylsulfonyl)ethanamineHCID 568513565-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride

Product 1

HCID 57597145N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-N'-[2-(methylsulfonyl)ethyl]urea

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

5-(2-Aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (54.1 mg) and triethylamine (0.7 mL) were dissolved in dichloromethane (10 mL), 1,1′-carbonylbis(1H-imidazole) was added, and the mixture was stirred at room temperature. After 1 hr, 2-(methylsulfonyl)ethanamine (1.0 mL) was added, and the mixture was further stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate and concentrated, and the residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=90:10). crystallized from diethyl ether/ethyl acetate/hexane to give the title compound (37.6 mg).

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. temperaturecooling
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=90:10)
  8. customcrystallized from diethyl ether/ethyl acetate/hexane

Sources & evidence

ORD record
ord-50ea9b4fedde4ccf859e8dabc42545ce
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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