Trifluoroacetic acid → Trifluoroacetic acid

HRID 1748396Notes

Reaction equation

HRID 1748396 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([NH:19][CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[NH2:22][CH2:21][CH2:20][NH:19][C:17]([C:12]1[CH:13]=[N:14][C:15]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:6][CH2:5][C:4]1[CH:30]=[CH:31][CH:32]=[C:2]([Cl:1])[CH:3]=1)[CH:16]=2)=[O:18].[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131733288HCID 131733288, compound

Product 2

HCID 6422Trifluoroacetic acidYield 100%HCID 86296656HCID 86296656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution, 0° C., of tert-Butyl (2-(7-((3-chlorobenzyl)oxy)quinoline-3-carboxamido)ethyl)carbamate in DCM (1 mL) was added TFA (1 mL). The reaction was stirred for 1 hour, and concentrated under reduced pressure. The reaction mixture was taken up in MeOH and concentrated under reduced pressure to afford the title compound as a white solid, TFA salt (57 mg, 100%) 1H NMR (400 MHz, DMSO-d6) δ 9.22 (d, J=2.0 Hz, 1H), 8.88 (t, J=5.5 Hz, 1H), 8.76 (s, 1H), 8.03 (d, J=9.0 Hz, 1H), 7.60 (s, 1H), 7.54 (d, J=2.3 Hz, 1H), 7.51-7.39 (m, 4H), 5.34 (s, 2H), 3.55 (q, J=6.3 Hz, 2H), 3.10-2.95 (m, 2H). [M+H]=356.3

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-711106661237479abe89109c2ff6d63a
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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