Water → HCID 75044842, compound

HRID 1254939Notes

Reaction equation

HRID 1254939 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([OH:22])=O)=[CH:17][CH:18]=3)[CH2:13][O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:35]([N:37]([CH2:41][CH3:42])[CH2:38][CH2:39][NH2:40])[CH3:36].O>C1COCC1>[CH2:35]([N:37]([CH2:41][CH3:42])[CH2:38][CH2:39][NH:40][C:20]([C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[C:11](=[C:10]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]1=[O:1])[O:12][CH2:13]2)=[O:22])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 68995924HCID 68995924, compound

Product 1

HCID 75044842HCID 75044842, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-carboxylic acid (100 mg, 0.34 mmol) and 1,1′-carbonyldiimidazole (100 mg, 0.62 mmol) in THF (10 ml) was stirred at room temperature for 16 hours. N,N-diethylethylenediamine (0.25 ml, 1.76 mmol) was added. The mixture was stirred for 15 minutes and poured into water (100 ml). The precipitates were filtered, washed with water and dried under vacuum to give the title compound as a yellow powder (99 mg, 74%).

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-23e7e95d206848d0a6f818a239a70166
Source dataset
uspto-grants-2013_06
Patent number
US08455656B2

Reaction notes

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