Acetonitrile → HCID 18522191, compound

HRID 2306113Notes

Reaction equation

HRID 2306113 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[C:34]([NH:35]C)=[CH:33][CH:32]=[C:31]2[C:10]=1[C:11](=[O:37])[O:12][C:13]12[C:26]2[CH:25]=[C:24]([F:27])[C:23]([OH:28])=[CH:22][C:21]=2[O:20][C:19]2[C:14]1=[CH:15][C:16]([F:30])=[C:17]([OH:29])[CH:18]=2.[C:38]([O-:41])([O-])=O.[Cs+].[Cs+].[C:44](#N)C>>[NH2:8][C:9]1[C:34]([NH2:35])=[CH:33][CH:32]=[C:31]2[C:10]=1[C:11](=[O:37])[O:12][C:13]12[C:14]2[CH:15]=[C:16]([F:30])[C:17]([O:29][C:1](=[O:3])[CH3:2])=[CH:18][C:19]=2[O:20][C:21]2[C:26]1=[CH:25][C:24]([F:27])=[C:23]([O:28][C:38](=[O:41])[CH3:44])[CH:22]=2

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 10796Cesium carbonateHCID 10431792DAF-FM

Product 1

HCID 18522191HCID 18522191, compound

Procedure

Acetic anhydride (52 ml, 0.55 mmol) was added to DAF-FM (94 mg, 0.23 mmol) and Cs2CO3 (84 mg, 0.26 mmol) suspended in acetonitrile (20 ml), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (84 mg, 75%). The product was further recrystallized from 2-isopropanol to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (84 mg, 75%)
  3. customThe product was further recrystallized from 2-isopropanol

Sources & evidence

ORD record
ord-ce746746990849ad84f2240f1515fd6e
Source dataset
uspto-grants-2002_08
Patent number
US06441197B1

Reaction notes

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