Dichloromethane → Diisopropylethylamine

HRID 2307309Notes

Reaction equation

C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl[CH2:9]Cl.O1[CH2:15][CH2:14][CH2:13]C1>>[CH:14]([N:3]([CH:4]([CH3:5])[CH3:9])[CH2:6][CH3:7])([CH3:15])[CH3:13]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

Product 1

HCID 81531Diisopropylethylamine

Procedure

A tricyclic benzodiazepine of formula (1) is treated with an appropriately substituted haloaroyl (heteroaroyl) halide, preferably a fluoro aroyl or a fluoro (or chloro) heteroaroyl chloride of formula (29), in the presence of a base such as triethylamine or diisopropylethylamine in an aprotic organic solvent such as dichloromethane or tetrahydrofuran at temperatures from −40° C. to the reflux temperature of the solvent to yield the acylated derivative (30).

Sources & evidence

ORD record: ord-c5d041298c3848c88fcb92f869115dfe
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831079B1

Reaction notes

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