trans-1,2,3,4,4a,5,6,10b-Octahydro-benzo[f]quinoline → HCID 178519359, compound

HRID 521035Notes

Reaction equation

HRID 521035 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH2:13]1[C@@H:22]2[C@H:17]([CH2:18][CH2:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=32)[NH:16][CH2:15][CH2:14]1.C(Cl)Cl.CO>O>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:16]3[C@@H:17]4[C@H:22]([C:21]5[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=5[CH2:19][CH2:18]4)[CH2:13][CH2:14][CH2:15]3)=[O:12])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11030553trans-1,2,3,4,4a,5,6,10b-Octahydro-benzo[f]quinolineHCID 21226129Dichloromethane methanolHCID 178524171HCID 178524171, compound

Product 1

HCID 178519359HCID 178519359, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared from 1H-benzoimidazole-5-carboxylic acid and trans-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline following a procedure analogous to that described in Example 1. Yield: 31% of theory; TLC: rf=0.40 (silica gel, CH2Cl2/MeOH/32% aqueous NH3 90:10:1); Mass spectrum (ESI+): m/z=332 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 1.32-1.46 (m, 1H), 1.53-1.76 (m, 2H), 2.14-2.24 (m, 1H), 2.30-2.43 (m, 1H), ca. 2.49-2.56 superimposed by D3CSOCHD2 signal (m, 1H), 2.77-2.93 (m, 2H), 3.03-3.13 (m, 1H), ca. 3.25-3.34 superimposed by H2O signal (m, 1H), 3.34-3.43 (m, 1H), 3.67-3.76 (m, 1H), 7.07-7.19 (m, 3H), 7.26-7.32 (m, 2H), 7.59-7.70 (m, 2H), 8.30 (s, 1H), 12.60 (broad s, 1H).

Sources & evidence

ORD record
ord-688c1e4253404a1db27661ba5c44de5e
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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