Dimethylformamide → 10-Chloro-2-(2-fluoroethyl)-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

HRID 2234434Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]2[C:10](=[CH:11][N:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH2:7][CH2:6][N:5]2[CH2:15][C:16]#C.BrCC[F:21].CN(C=O)C>>[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([N:9]([CH3:13])[C:8](=[O:14])[CH2:7][CH2:6][N:5]2[CH2:15][CH2:16][F:21])=[CH:11][N:12]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 129822-Fluoroethyl bromide

HCID 866175499-Chloro-2-methyl-6-prop-2-ynyl-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-3-one

Product 1

HCID 8661755310-Chloro-2-(2-fluoroethyl)-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

Procedure

The title compound was prepared by an analogous method to the preparation of Intermediate 154, on a 0.31 mmol scale, utilising 1-bromo-2-fluoroethane (Apollo Scientific; 235 mg, 1.44 mmol), as a white crystalline solid containing 0.6 equivalents of DMF (86 mg, 100%).

Sources & evidence

ORD record: ord-314c620992a34007ad9f96927caab690
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709471B2

Reaction notes

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