HCID 10798140, compound → HCID 178421262, compound

HRID 521042Notes

Reaction equation

HRID 521042 reaction equation
N1C2C=CC(C(O)=O)=CC=2N=C1.C[C@@]12C3C=CC=CC=3CC[C@@H]1NCCC2.C[C@]12C3C=CC=CC=3CC[C@@H]1NCCC2.[NH:43]1[C:47]2[CH:48]=[CH:49][C:50]([C:52]([N:54]3[C@@H:63]4[C@@:58]([CH3:68])([C:59]5[CH:67]=[CH:66][CH:65]=[CH:64][C:60]=5[CH2:61][CH2:62]4)[CH2:57][CH2:56][CH2:55]3)=[O:53])=[CH:51][C:46]=2[N:45]=[CH:44]1>>[NH:43]1[C:47]2[CH:48]=[CH:49][C:50]([C:52]([N:54]3[C@@H:63]4[C@:58]([CH3:68])([C:59]5[CH:67]=[CH:66][CH:65]=[CH:64][C:60]=5[CH2:61][CH2:62]4)[CH2:57][CH2:56][CH2:55]3)=[O:53])=[CH:51][C:46]=2[N:45]=[CH:44]1

Participants

5

Reactant 4

HCID 10798140HCID 10798140, compoundHCID 67201248HCID 67201248, compoundHCID 178421263HCID 178421263, compoundHCID 178524171HCID 178524171, compound

Product 1

HCID 178421262HCID 178421262, compoundYield 15%

Procedure

The title compound is prepared from 1H-benzoimidazole-5-carboxylic acid and an isomeric mixture of cis-10b-methyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline and trans-10b-methyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline following a procedure analogous to that described in Example 1 yielding a mixture of Example 10 and Example 11 which is separated by HPLC on reversed phase (MeOH/H2O/NH4OH). Yield: 15% of theory; LC (method 2): tR=3.26 min; Mass spectrum (ESI+): m/z=346 [M+H]+.

Workup

  1. customis separated by HPLC on reversed phase (MeOH/H2O/NH4OH)

Sources & evidence

ORD record
ord-399ffb519f224c9da021ec595fd9e218
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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