Acrylonitrile → HCID 118159750, compound

HRID 628424Notes

Reaction equation

HRID 628424 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].FC(F)(F)C(O)=O.[N:22]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:49]=[CH:50][CH:51]=2)[CH2:30][N:31]2[C:35]3[CH:36]=[CH:37][C:38]4[N:39]([C:40]([CH3:43])=[N:41][N:42]=4)[C:34]=3[CH:33]=[C:32]2[C:44]2[CH:48]=[CH:47][NH:46][N:45]=2)[CH2:25][CH2:24][CH2:23]1.[C:52](#[N:55])[CH:53]=[CH2:54].N12CCCN=C1CCCCC2>CC#N>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[N:22]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:49]=[CH:50][CH:51]=2)[CH2:30][N:31]2[C:35]3[CH:36]=[CH:37][C:38]4[N:39]([C:40]([CH3:43])=[N:41][N:42]=4)[C:34]=3[CH:33]=[C:32]2[C:44]2[CH:48]=[CH:47][N:46]([CH2:54][CH2:53][C:52]#[N:55])[N:45]=2)[CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178433847HCID 178433847, compound

Product 1

HCID 118159750HCID 118159750, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-[3-(Azetidin-1-ylmethyl)benzyl]-1-methyl-7-(1H-pyrazol-3-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (7.0 mg, 0.018 mmol, from Example 182) in MeCN (0.23 mL) was treated with 2-propenenitrile (2.3 μL, 0.035 mmol, Aldrich) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 μL, 0.018 mmol, Aldrich) for 8 minutes. The product was purified via preparative HPLC-MS (Waters SunFire C18, eluting with a gradient of MeCN/H2O containing 0.1% TFA). Yield: (9.8 mg, 82%).

Workup

  1. customThe product was purified via preparative HPLC-MS (Waters SunFire C18
  2. washeluting with a gradient of MeCN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-d482172bb0cd4bc88f77cc0d02800ce6
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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