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Ethyl Bromide → HCID 68906101, compound

HRID 729508
Notes
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Reaction equation

HRID 729508 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1.Br[CH2:33][CH3:34].C([O-])([O-])=O.[K+].[K+]>CC#N.C(Cl)Cl>[CH2:33]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH3:25])[CH:18]=2)[N:9]=1)[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 68905806{4-[5-(2,5-Diaza-bicyclo[2.2.1]hept-2-yl)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine

Product 1

HCID 68906101HCID 68906101, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

The mixture of 50 mg (0.12 mmol) {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-imidazo [1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine in 20 mL CH3CN was treated with 26 mg (0.24 mmol) bromoethane and 33 mg (0.24 mmol) K2CO3. The mixture was stirred at rt for 15 h. MS showed all starting materials were converted. The mixture was diluted with 50 mL DCM, washed with 20 mL sat. NaHCO3, dried over anhydrous Na2SO4. After purification by chromatography, obtained the title compound in 20 mg as a yellow solid. MS (ES+): 440 (M+H)+.

Workup

  1. washwashed with 20 mL sat. NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter purification by chromatography

Sources & evidence

ORD record
ord-0154b181e3fa4c798bb96ba29c81cb3a
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582631B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes