Hydracrylonitrile → HCID 66924315, compound

HRID 1360201Notes

Reaction equation

HRID 1360201 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]3[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]4[NH:22][CH:23]=[CH:24][C:14]=34)[CH2:3]1)[CH2:9]2.[CH2:25]([C:28]#[N:29])[CH2:26][OH:27]>C(N(CC)CC)C>[C:28]([CH2:25][CH2:26][O:27][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]3[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=[C:15]4[NH:22][CH:23]=[CH:24][C:14]=34)[CH2:3]1)[CH2:9]2)#[N:29]

Participants

4

Reactant 2

HCID 8011HydracrylonitrileHCID 66924080HCID 66924080, compound

Product 1

HCID 66924315HCID 66924315, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 4-[(5-bromoadamantan-2-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (52 mg) were added ethylene cyanhydrin (250 μl) and triethylamine (56 μl), and the mixture was stirred for 20 minutes using a microwave reaction system at 150° C. The reaction solution was cooled and purified by silica gel column chromatography (chloroform:methanol). The obtained fraction was concentrated under reduced pressure, and water was added. The obtained solid was collected by filtration to obtain 4-{[5-(2-cyanoethoxy)adamantan-2-yl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (16 mg).

Workup

  1. customa microwave reaction system at 150° C
  2. temperatureThe reaction solution was cooled
  3. custompurified by silica gel column chromatography (chloroform:methanol)
  4. concentrationThe obtained fraction was concentrated under reduced pressure, and water
  5. additionwas added
  6. filtrationThe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-8798ff82741442f4a146fb35a9f013c9
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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