1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68453166, compound

HRID 2355064Notes

Reaction equation

HRID 2355064 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[F:11][C:12]([F:26])([F:25])[C:13]1[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=1[O:15][C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1.C1CCN2C(=NCCC2)CC1>O1CCOCC1.O>[F:26][C:12]([F:11])([F:25])[C:13]1[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=1[O:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:2]2[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=2)[CH2:17]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2773502Methyl 2-bromothiazole-5-carboxylateHCID 26191991(3S)-3-[2-(Trifluoromethyl)phenoxy]pyrrolidine

Product 1

HCID 68453166HCID 68453166, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-bromo-1,3-thiazole-5-carboxylate (2.101 g, 9.46 mmol), (3S)-3-[2-(trifluoromethyl)phenoxy]pyrrolidine (2 g, 8.7 mmol) and DBU (2.7 mL, 17.9 mmol) in dioxane (30 mL) was heated at 80° C. for 24 h. After cooling, the mixture was diluted with water and extracted twice with EtOAc. The combined EtOAc extracts were washed with water, dried and concentrated. Combi-Flash chromatography (120 g, 40-80% EtOAc in hexanes in 20 min, 70 mL/min, 25 mL/fraction) gave the title compound as a white solid. 1H NMR (400 MHz, acetone-d6): δ 7.84 (s, 1 H), 7.67 (m, 2 H), 7.41 (d, 1 H), 7.17 (t, 1 H), 5.51 (s, 1 H), 3.95 (m, 1 H), 3.80-3.65 (m, 6 H), 2.60-2.46 (m, 2 H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with EtOAc
  3. washThe combined EtOAc extracts were washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcf8e8e5c1394773b6c9886a5ed30145
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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