Trifluoroacetic acid → HCID 66774074, compound

HRID 1644465Notes

Reaction equation

HRID 1644465 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[C:21]([C:27]#[N:28])[CH:22]=[C:23]([F:26])[CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:29])[CH2:10][CH2:9]1)(C)(C)C.C(OC(=O)NC1CCN(CCN2C3C(=C(F)C=C(C#N)C=3)C=CC2=O)CC1)(C)(C)C.FC(F)(F)C(O)=O.NC1CCN(CCN2C3C(=CC=C(F)C=3)N=CC2=O)CC1>ClCCl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:24](=[C:23]([F:26])[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=3)[CH:19]=[CH:18][C:17]2=[O:29])[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 593979071-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-oneHCID 86642653HCID 86642653, compound2×HCID 86664538HCID 86664538, compound

Product 1

HCID 66774074HCID 66774074, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl{1-[2-(5-cyano-7-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate and tert-butyl{1-[2-(7-cyano-5-fluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediates 173 and 174, 170 mg, 0.41 mmol) was reacted with trifluoroacetic acid in dichloromethane as described for Intermediate 140 to give 120 mg (92% yield) of the mixture of regioisomers as an oil. This mixture was carried on without further purification to the next step.

Sources & evidence

ORD record
ord-ce8e25b20099445c856938d5826f6a3d
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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