Water → HCID 67278197, compound

HRID 1696248Notes

Reaction equation

HRID 1696248 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]3[C:19]4=[C:20]5[CH:26]=[CH:25][NH:24][C:21]5=[N:22][CH:23]=[C:18]4[NH:17][C:16]3=[O:27])[CH2:9]2)[CH:5]=[CH:4][N:3]=1.[C-]#N.[Na+].[N:31]12CCN(CC1)C[CH2:32]2.O>CS(C)=O>[CH3:14][C@@H:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:32]#[N:31])[N:7]=2)[CH2:9][C@@H:10]1[N:15]1[C:19]2=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=[C:18]2[NH:17][C:16]1=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 9237DabcoHCID 87336222HCID 87336222, compound

Product 1

HCID 67278197HCID 67278197, compoundYield 245.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of rel-1-[(3R,4R)-1-(2-chloro-4-pyrimidinyl)-4-methyl-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]-pyridin-2(1H)-one (60 mg) and sodium cyanide (38 mg) in DMSO (1 mL), 1,4-diazabicyclo[2.2.2]octane (5 mg) was added at ambient temperature. The temperature was raised to 80° C. and stirred for 7 hours. After cooling down to ambient temperature, water (15 mL) was added to the mixture and resulting precipitate was collected by filtration. The filtrate was purified by pre-packed column (chloroform:methanol=95:1 to 80:20) to afford rel-4-[(3R,4R)-4-methyl-3-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(2H)-yl)-1-piperidinyl]-2-pyrimidinecarbonitrile (41 mg) as white powder.

Workup

  1. temperatureAfter cooling down to ambient temperature
  2. customresulting precipitate
  3. filtrationwas collected by filtration
  4. customThe filtrate was purified by pre-packed column (chloroform:methanol=95:1 to 80:20)

Sources & evidence

ORD record
ord-31bf9d0c3220485297ae5e1db75fa5bc
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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