HCID 10798140, compound → HCID 178421263, compound

HRID 521041Notes

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.[CH3:13][C@@:14]12[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C@@H:19]1[NH:18][CH2:17][CH2:16][CH2:15]2.C[C@]12C3C=CC=CC=3CC[C@@H]1NCCC2>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:18]3[C@@H:19]4[C@@:14]([CH3:13])([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[CH2:21][CH2:20]4)[CH2:15][CH2:16][CH2:17]3)=[O:12])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Reactant 3

HCID 10798140HCID 10798140, compound

HCID 67201248HCID 67201248, compound

HCID 178524171HCID 178524171, compound

Product 1

HCID 178421263HCID 178421263, compoundYield 20%

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: 20% of theory; LC (method 2): tR=3.40 min; Mass spectrum (ESI+): m/z=346 [M+H]+; 1H NMR (400 MHz, DMSO-d6, mixture of 2 rotamers) δ 1.33 (s, 3H), 1.42-1.53 (m, 2H), 1.62-1.78 (m, 1H), 2.15-2.23 (m, 1H), 2.27-2.35 (m, 1H), 2.75-2.90 (m, 3H), 3.07-3.18 (m, 1H), 3.43-3.49 (m, 1H), 3.69-3.77 (m, 1H), 7.04-7.18 (m, 3H), 7.20-7.34 (m, 2H), 7.56 (broad s, 0.75H), 7.58 (broad s, 0.25H), 7.67 (broad s, 0.75H), 7.69 (broad s, 0.25H), 8.29 (s, 1H), 12.53-12.62 (m, 1H).

Workup

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

Sources & evidence

ORD record: ord-88c2b03b887c4290821afbe2f1afdba1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328072B2

Reaction notes

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