2-(3-(methylamino)propyl)-1H-benzimidazole → rac-(1R,8R,9R*)-9-(2-{[3-(1H-Benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol

HRID 1879351Notes

Reaction equation

[OH:1][C@@:2]1([CH2:14][CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:11][C@H:10]2[CH2:12][CH2:13][C@@H:3]1[C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[CH2:36][CH2:37][CH2:38][NH:39][CH3:40]>CCN(C(C)C)C(C)C>[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[CH2:36][CH2:37][CH2:38][N:39]([CH3:40])[CH2:15][CH2:14][C:2]1([OH:1])[CH2:11][CH:10]2[CH2:12][CH2:13][CH:3]1[C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1000 mg of rac-toluene-4-sulfonic acid (1R*,8R*,9R*)-2-(9-hydroxy-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)ethyl ester and 508 mg of [3-(1H-benzoimidazol-2-yl)-propyl]-methyl-amine in 2 mL of DIPEA was heated to 110° C. for 30 min. The reaction mixture was cooled to rt, quenched with MeOH-water and extracted with EtOAc. The organic phase was separated, dried over Na2SO4 and concentrated in vacuo to obtain 1.0 g as beige solid. A part of the crude product was purified by CC with EtOAc/MeOH (2:1) to obtain the desired compound as beige foam.

Workup

temperatureThe reaction mixture was cooled to rt
customquenched with MeOH-water
extractionextracted with EtOAc
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto obtain 1.0 g as beige solid
customA part of the crude product was purified by CC with EtOAc/MeOH (2:1)

Sources & evidence

ORD record: ord-2a1b1248cc314fc5adfe330f093e79c9
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314253B2

Reaction notes

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