1,1'-Carbonyldiimidazole → HCID 178518918, compound

HRID 911881Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([NH:18][NH2:19])=[O:17])[N:13]=2)=[N:6][CH:7]=1.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[O:17][C:32]([OH:33])=[N:19][N:18]=3)[N:13]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide (0.150 g, 0.345 mmol) in THF (5 mL) was added TEA (0.04814 mL, 0.3454 mmol) and cooled in an ice bath. To this mixture was added. CDI (0.0672 g, 0.414 mmol) in one portion. The mixture was allowed to warn to ambient temperature and was then heated at 50° C. overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2 and washed with water, dried over Na2SO4, concentrated to a residue that was purified by preparative HPLC to give the title compound (0.045 g, 28.31% yield) was white solids. 1H NMR (d6DMSO) δ 2.91 (s, 4H), 6.75 (s, 1H), 7.10 (d, J=7.8 Hz, 2H), 7.21 (t, J=7.4 Hz, 1H), 7.40 (d, J=2.1 Hz, 1H), 7.44 (t, J=7.9 Hz, 2H), 8.22 (d, J=2.1 Hz, 1H), 11.03 (br s, 1H), 12.04 (br s, 1H).

Workup

temperaturecooled in an ice bath
additionTo this mixture was added
customto warn to ambient temperature
concentrationThe reaction was concentrated to dryness
dissolutiondissolved in CH2Cl2
washwashed with water
dry with materialdried over Na2SO4
concentrationconcentrated to a residue that
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-3bab2147a3a34d1d86ad2f2c02797e6e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022223B2

Reaction notes

Loading…