Acetonitrile → HCID 18522191, compound

HRID 413882Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].C[NH:9][C:10]1[CH:15]=[CH:14][C:13]2[C:16]3([O:34][C:35](=[O:36])[C:12]=2[C:11]=1[NH2:37])[C:29]1[C:24](=[CH:25][C:26]([OH:31])=[C:27]([F:30])[CH:28]=1)[O:23][C:22]1[C:17]3=[CH:18][C:19]([F:33])=[C:20]([OH:32])[CH:21]=1.[C:38]([O-:41])([O-])=O.[Cs+].[Cs+].[C:44](#N)C>>[NH2:37][C:11]1[C:10]([NH2:9])=[CH:15][CH:14]=[C:13]2[C:12]=1[C:35](=[O:36])[O:34][C:16]12[C:17]2[CH:18]=[C:19]([F:33])[C:20]([O:32][C:1](=[O:3])[CH3:2])=[CH:21][C:22]=2[O:23][C:24]2[C:29]1=[CH:28][C:27]([F:30])=[C:26]([O:31][C:38](=[O:41])[CH3:44])[CH:25]=2

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 7918Acetic Anhydride

HCID 10796Cesium carbonate

HCID 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

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

Sources & evidence

ORD record: ord-bc05add7da7d4e37b4a785589491d8e7
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06569892B2

Reaction notes

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