1,1'-Carbonyldiimidazole → HCID 57329938, compound

HRID 1054091Notes

Reaction equation

HRID 1054091 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[CH:10][C:9]([CH:12]([OH:16])[CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=2)=[CH:2]1.[CH:17]1[N:21]=[CH:20][N:19]([C:22](N2C=NC=C2)=[O:23])[CH:18]=1>C(#N)C>[N:19]1([C:22]([O:16][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)[CH:13]([CH3:14])[CH3:15])=[O:23])[CH:18]=[CH:17][N:21]=[CH:20]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67511585HCID 67511585, compound

Product 1

HCID 57329938HCID 57329938, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 49a (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)=0.92 (d, J=6.9 Hz, 3H), 1.11 (d, J=6.3 Hz, 3H), 2.25-2.44 (m, 1H), 5.63 (d, J=7.9 Hz, 1H), 6.88 (s, 1H), 7.08 (s, 1H), 7.41-7.58 (m, 3H), 7.66 (dd, J=7.9, 1.9 Hz, 1H), 8.03 (s, 1H), 8.16 (s, 1H), 8.60 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.6, 18.8, 33.5, 83.8, 108.7, 117.2, 120.0, 126.8, 131.1, 131.4, 135.4, 137.2, 141.7, 144.2, 148.2, 148.8, 152.5; MS (ESI): m/z=312.32 [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-78d646372ba241f58c227dd539633b0c
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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