1,1'-Carbonyldiimidazole → HCID 71264269, compound

HRID 1506246Notes

Reaction equation

HRID 1506246 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][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1.[C:34](N1C=CN=C1)(N1C=CN=C1)=[O:35]>ClCCl>[CH2:27]([N:24]1[CH2:23][CH2:22][CH:21]([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]([CH3:17])([CH3:18])[CH3:19])[C:6]=4[N:7]=[CH:8][C:3]=3[CH2:2][NH:1][C:34]2=[O:35])[CH2:26][CH2:25]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 71258235HCID 71258235, compound

Product 1

HCID 71264269HCID 71264269, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Aminomethyl)-N-(1-benzylpiperidin-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine (38 mg, 0.081 mmol) in dichloromethane was stirred with 1,1′-carbonyldiimidazole (20.0 mg, 0.123 mmol) at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and, after addition of water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v)) to give the title compound (30.9 mg, yield 77%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v))

Sources & evidence

ORD record
ord-3259a0a8c5c04ef4a117e3e316bb6c65
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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