1,1'-Carbonyldiimidazole → HCID 57329873, compound

HRID 1054087Notes

Reaction equation

HRID 1054087 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[CH:10][C:9]([CH:12]([OH:14])[CH3:13])=[CH:8][CH:7]=2)=[CH:2]1.[CH:15]1[N:19]=[CH:18][N:17]([C:20](N2C=NC=C2)=[O:21])[CH:16]=1>C(#N)C>[N:17]1([C:20]([O:14][CH:12]([C:9]2[CH:10]=[N:11][C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)=[CH:7][CH:8]=2)[CH3:13])=[O:21])[CH:16]=[CH:15][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67511005HCID 67511005, compound

Product 1

HCID 57329873HCID 57329873, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 47a (110 mg, 0.58 mmol), CDI (471 mg, 2.91 mmol) and acetonitrile (7 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (3:2) as eluent. White solid. Yield: 40 mg, 24%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.78 (d, J=6.6 Hz, 3H), 6.11 (q, J=6.7 Hz, 1H), 6.89 (dd, J=1.9, 0.9 Hz, 1H), 7.07 (dd, J=1.6, 0.6 Hz, 1H), 7.40-7.44 (m, 1H), 7.46-7.52 (m, 2H), 7.74 (dd, J=8.4, 2.7 Hz, 1H), 8.04 (dd, J=1.4, 0.8 Hz, 1H), 8.12-8.18 (m, 1H), 8.67 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=21.4, 74.9, 108.5, 117.0, 119.9, 126.5, 130.8, 132.8, 134.6, 137.0, 141.6, 144.0, 147.9, 148.0, 152.4; MS (ESI): m/z=284.25 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (3:2) as eluent

Sources & evidence

ORD record
ord-017fb3db8edf4d16b2647d37cc8ad4a1
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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