1,1'-Carbonyldiimidazole → HCID 57329873, compound

HRID 1054089Notes

Reaction equation

HRID 1054089 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[CH:10][C:9]([CH:12]([OH:15])[CH2:13]C)=[CH:8][CH:7]=2)=[CH:2]1.[CH:16]1[N:20]=[CH:19][N:18]([C:21](N2C=NC=C2)=[O:22])[CH:17]=1>C(#N)C>[N:18]1([C:21]([O:15][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:22])[CH:17]=[CH:16][N:20]=[CH:19]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67511306HCID 67511306, compound

Product 1

HCID 57329873HCID 57329873, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 48a (73.0 mg, 0.36 mmol), CDI (291 mg, 1.80 mmol) and acetonitrile (4 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:1) as eluent. Green oil. Yield: 62 mg, 67%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.00 (t, J=7.4 Hz, 3H), 1.96-2.08 (m, 1H), 2.12-2.24 (m, 1H), 5.85 (t, J=7.1 Hz, 1H), 6.88 (dd, J=1.9, 0.6 Hz, 1H), 7.04-7.09 (m, 1H), 7.42 (t, J=1.4 Hz, 1H), 7.45-7.51 (m, 2H), 7.69 (dd, J=8.2, 2.2 Hz, 1H), 8.01-8.06 (m, 1H), 8.15 (s, 1H), 8.63 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=9.7, 28.6, 79.8, 108.5, 117.0, 119.8, 126.5, 130.7, 131.8, 134.9, 136.9, 141.5, 144.0, 148.0, 148.3, 152.3; MS (ESI): m/z=298.27 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-e6c13269a52c4142a1b4e2e3102807ae
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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