1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178492073, compound

HRID 2376235Notes

Reaction equation

HRID 2376235 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][C@H:23]([C:31]3[N:35](CCC#N)[N:34]=[N:33][N:32]=3)[C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C1CCN2C(=NCCC2)CC1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11]([CH2:22][C@H:23]([C:31]3[NH:35][N:34]=[N:33][N:32]=3)[C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68993431HCID 68993431, compound

Product 1

HCID 178492073HCID 178492073, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(5-{(S)-2-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-1-m-tolyl-ethyl}-tetrazol-1-yl)-propionitrile (1.5 g, 2.7 mmol) in dichloromethane (25 mL) was added DBU (2.9 mL, 18.9 mmol, 7.0 equiv), and the mixture was stirred at room temperature for 48 h. Dichloromethane (200 mL) was added, and the resulting mixture was washed with 1 N HCl (2×100 mL) then water (100 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude residue was purified by flash chromatography (50% dichloromethane/ethyl acetate) to afford the title compound (1.3 grams, 95%). HPLC: Rt=5.31 (Method A). MS (ESI): mass calculated for C26H22Cl2N6O, 504.12; m/z found, 505.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.32 (d, J=8.2 Hz, 1H), 7.28-7.24 (m, 3H), 7.21 (t, J=7.7 Hz, 1H), 7.15 (d, J=8.8 Hz, 2H), 7.08 (d, J=7.7 Hz, 1H), 6.95-6.94 (m, 3H), 6.88 (dd, J=8.5, 2.2 Hz, 1H), 6.18 (s, 1H), 4.85 (dd, J=9.0, 3.6 Hz, 1H), 3.86 (s, 3H), 3.58 (dd, J=14.8, 8.5 Hz, 1H), 3.42 (dd, J=15.4, 3.6 Hz, 1H), 2.31 (s, 3H).

Workup

  1. washthe resulting mixture was washed with 1 N HCl (2×100 mL)
  2. dry with materialwater (100 mL), dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by flash chromatography (50% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-3f766ae1097a40e0b69a53c18088cffc
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

Loading…