Acrylonitrile → HCID 118159829, compound

HRID 628333Notes

Reaction equation

HRID 628333 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][C:13]([N:17](C(OC(C)(C)C)=O)[NH:18]C(OC(C)(C)C)=O)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:33]1[N:34]=[CH:35][N:36]([C:38](C2C=CC=CC=2)(C2C=CC=CC=2)[C:39]2C=CC=C[CH:40]=2)[CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:57](#N)[CH:58]=C.[N:61]12CCCN=C1CCCCC2>CC#N>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]3[N:12]([C:57]([CH3:58])=[N:18][N:17]=3)[C:11]=2[CH:10]=[C:9]1[C:33]1[N:34]=[CH:35][N:36]([CH2:38][CH2:39][C:40]#[N:61])[CH:37]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 118159532HCID 118159532, compound

Product 1

HCID 118159829HCID 118159829, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-benzyl-7-(1H-imidazol-4-yl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (4.3 mg, 0.013 mmol, from Example 74) and 2-propenenitrile (2.6 μL, 0.039 mmol, Aldrich) in MeCN (0.17 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.0 μL, 0.013 mmol, Aldrich). The reaction was allowed to proceed for 15 minutes, then was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (3.3 mg, 66%).

Workup

  1. customwas purified via preparative HPLC-MS (C18
  2. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-2eeee7dac89c4bdcbc6e4ff4b5b51cfb
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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