Ammonia → HCID 178513601, compound

HRID 2360879Notes

Reaction equation

HRID 2360879 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[C@@H:21]4[C@@H:16]([C:17]5[C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=[CH:22][C:18]=5[CH2:19][CH2:20]4)[CH2:15][CH2:14][CH2:13]3)=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH3:29]>C(Cl)Cl.CO>[NH:1]1[C:5]2[CH:4]=[CH:9][C:8]([C:10]([N:12]3[C@@H:21]4[C@@H:16]([C:17]5[C:25]([C:26]([NH2:29])=[O:28])=[CH:24][CH:23]=[CH:22][C:18]=5[CH2:19][CH2:20]4)[CH2:15][CH2:14][CH2:13]3)=[O:11])=[CH:7][C:6]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178524200HCID 178524200, compound

Product 1

HCID 178513601HCID 178513601, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound is prepared from cis-4-(1H-benzoimidazole-5-carbonyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-10-carboxylic acid and ammonia (7 mol/L in methanol) following a procedure analogous to that described in Example 1. Yield: 58% of theory; TLC: rf=0.24 (silica gel, CH2Cl2/MeOH/32% aqueous NH3 90:10:1); Mass spectrum (ESI+): m/z=375 [M+H]+.

Sources & evidence

ORD record
ord-bce39bc8da164eed891505129b01e4bb
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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