1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(7-Hydroxy-2-benzothiazolyl)-3-ethyl-urea

HRID 9110Notes

Reaction equation

Br[C:2]1(Br)[CH2:16][CH2:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]1=[O:17].C1CCN2C(=NCCC2)CC1>C1COCC1>[OH:17][C:3]1[C:4]2[S:8][C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])=[N:6][C:5]=2[CH:15]=[CH:16][CH:2]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 1-(6-bromo-7-oxo-4,5,6,7-tetrahydro-2-benzothiazolyl)-3-ethyl-urea 5 (0.100 g, 0.314 mmol) in THF (1.0 mL) was added DBU (0.141 mL, 0.94 mmol, 3 eq) dropwise at about 20° C. A dark green suspension was obtained while heat was generated upon addition of DBU. It was stirred at about 20° C. for about 18 hours. The reaction mixture was concentrated and dissolved in DMF (2 mL). LC/MS purification gave 0.024 g (32%) of the desired compound 8. 1H NMR (DMSO) δ 10.54 (br s, 1H, NH), 7.17–7.07 (m, 2H, ArH), 6.63 (d, 1H, J=6.9 Hz, ArH), 6.70 (br s, 1H, NH), 3.18 (m, 2H, CH2), 1.09 (t, 3H, J=7.2 Hz, CH3). LC/MS 238 (MH+); RP-HPLC RT 2.26 minutes.

Workup

customA dark green suspension was obtained
temperaturewhile heat
concentrationThe reaction mixture was concentrated
dissolutiondissolved in DMF (2 mL)
customLC/MS purification

Sources & evidence

ORD record: ord-f28c76dea7f44a58b87eb28465351440
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

Loading…