Dimethylformamide → HCID 21190779, compound

HRID 1068844Notes

Reaction equation

HRID 1068844 reaction equation
CN(C=O)C.O=[C:7]1[CH2:12][CH2:11][CH:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[N:19]=3)=[C:16]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:15]=[CH:14]2)[CH2:9][CH2:8]1>CCOCC>[CH:10]1([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[N:19]=3)=[C:16]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:15]=[CH:14]2)[CH2:9][CH2:8][CH2:7][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 10090302HCID 10090302, compound

Product 1

HCID 21190779HCID 21190779, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of the preceding example, DMF (10 mL), the product of example 1 (b) (1.59 g, 5.5 mmol) and KCO3 (0.308 g, 2.23 mmol) were combined and stirred for 2 days, diluted with Et2O and filtered. The filtrate was concentrated under high vacuum to a brown paste. Trituration with Et2O and hexane (1:1, 200 mL) afforded the title compound as a tan solid. Crystallization from EtOAc/hexane (1:4) afforded 0.631 g (39% from the product of example 1(d). ESP+ (Mass Spec) m/z 353 (MH+). mp=207-208.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under high vacuum to a brown paste

Sources & evidence

ORD record
ord-c81ead80804748b483924bb9d853ae70
Source dataset
uspto-grants-2001_06
Patent number
US06251914B1

Reaction notes

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