HCID 86654143, compound → HCID 178519362, compound

HRID 2272096Notes

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]([C:20]1[CH:33]=[CH:32][C:23]2[C@@H:24]3[C@H:29]([CH2:30][CH2:31][C:22]=2[CH:21]=1)[NH:28][CH2:27][CH2:26][CH2:25]3)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(CC2C=CC3[C@@H]4[C@H](CCC=3C=2)NCCC4)CCCCC1>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:28]3[C@@H:29]4[C@@H:24]([C:23]5[CH:32]=[CH:33][C:20]([CH2:13][CH:14]6[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]6)=[CH:21][C:22]=5[CH2:31][CH2:30]4)[CH2:25][CH2:26][CH2:27]3)=[O:12])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Reactant 3

HCID 86654143HCID 86654143, compound

HCID 86654144HCID 86654144, compound

HCID 178524171HCID 178524171, compound

Product 1

HCID 178519362HCID 178519362, compoundYield 50%

Procedure

The title compound is prepared from 1H-benzoimidazole-5-carboxylic acid and a mixture of cis-8-benzyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline and cis-8-cyclohexylmethyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline (ca. 30:70) following a procedure analogous to that described in Example 1 and separated from the also formed Example 82 by HPLC on reversed phase (MeOH/H2O/NH4OH). Yield: 50% of theory; LC (method 1): tR=4.06 min; Mass spectrum (ESI+): m/z=428 [M+H]+.

Workup

customseparated from the also formed Example 82 by HPLC on reversed phase (MeOH/H2O/NH4OH)

Sources & evidence

ORD record: ord-3b5fdfd1efa0479e95a7efe586255018
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120769B2

Reaction notes

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