1,1'-Carbonyldiimidazole → HCID 71264072, compound

HRID 1506200Notes

Reaction equation

HRID 1506200 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[N:7][C:6]2[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[CH:11][C:5]=2[C:4]=1[NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28]>ClCCl>[CH:21]1([N:20]2[C:4]3[C:5]4[CH:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:17])[CH3:18])[C:6]=4[N:7]=[CH:8][C:3]=3[CH2:2][NH:1][C:27]2=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 71258440HCID 71258440, compound

Product 1

HCID 71264072HCID 71264072, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Aminomethyl)-N-cyclohexyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine (127 mg, 0.339 mmol) in dichloromethane was stirred with 1,1′-carbonyldiimidazole (65.9 mg, 0.407 mmol) at 60° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and, after addition of water, extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound as a colorless oil (93.2 mg, yield 69%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of water
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-599b53385c5b4828a21fa0745203edd1
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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