2-Bromoethanol → HCID 22660615, compound

HRID 392776Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])=[CH:5]2.Br[CH2:20][CH2:21][OH:22].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:14][CH2:15][N:16]([CH2:20][CH2:21][OH:22])[CH2:17][CH2:18]1)=[O:12])=[CH:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

The product from Step B (1.0 g) was dissolved in CH3CN (10 mL) and treated with 2-bromoethanol (0.5 g) and then K2CO3 (0.8 g). The resulting mixture was heated at 60° C. overnight. The mixture was cooled to ambient temperature, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography (0-10% methanol/dichloromethane) to give the title compound (0.5 g). 1H NMR (400 MHz, CDCl3): δ 10.09 (br s, 1H), 7.61 (d, J=2.0 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 7.23 (dd, J=2.0, 8.8 Hz, 1H), 6.69 (d, J=0.8 Hz, 1H), 3.95 (br m, 3H), 3.72-3.69 (m, 2H), 2.67-2.64 (m, 4H), 2.52 (br s, 3H). MS (electrospray): exact mass calculated for C15H18ClN3O2, 307.78; m/z found, 308.1 [M+H]+.

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified via silica gel chromatography (0-10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-3ed1fc0c14c446faab33ca054a804788
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803362B2

Reaction notes

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