Trifluoroacetic acid methylene chloride → HCID 18689598, compound

HRID 1872470Notes

Reaction equation

HRID 1872470 reaction equation
C([O:5][C:6](=[O:49])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:48])[CH:16]([C:40]2[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=2)[N:17]2[CH:30]([CH2:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:29](=[O:38])[N:20]3[CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[CH2:28][CH:19]3[C:18]2=[O:39])=[CH:9][CH:8]=1)(C)(C)C.C(Cl)Cl.C(C(O)=O)(F)(F)F>>[C:46]([C:43]1[CH:44]=[CH:45][C:40]([CH:16]([N:17]2[CH:30]([CH2:31][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[C:29](=[O:38])[N:20]3[CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[CH2:28][CH:19]3[C:18]2=[O:39])[C:15]([NH:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:49])=[O:5])=[CH:12][CH:11]=2)=[O:48])=[CH:41][CH:42]=1)#[N:47]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 53901166HCID 53901166, compound

Product 1

HCID 18689598HCID 18689598, compoundYield 100%

Procedure

The above-described cyclized products 4-{[2-(4-cyano-phenyl)-2-(3-cyclohexylmethyl-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-2-yl)-acetylamino]-methyl}-benzoic acid tert-butyl ester (diastereomers A and B) were treated with a 1:1 CH2Cl2 /CF3CO2H solution according to General Method 3 to afford 27 mg (100%) of 4-{[2-(4-cyano-phenyl)-2-(3-cyclohexylmethyl-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-2-yl)-acetylamino]-methyl}-benzoic acid (diastereomer A) and 35 mg (100%) of 4-{[2-(4-cyano-phenyl)-2-(3-cyclohexylmethyl-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-2-yl)-acetylamino]-methyl}-benzoic acid (diastereomer B).

Sources & evidence

ORD record
ord-06ba45a17386498d874251dc1e22bf44
Source dataset
uspto-grants-2000_08
Patent number
US06107274

Reaction notes

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