Trifluoroacetic acid → HCID 58349431, compound

HRID 2090066Notes

Reaction equation

HRID 2090066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2[C:40]3[C:35](=[CH:36][C:37]([F:42])=[C:38]([F:41])[CH:39]=3)[N:34]=[CH:33][CH:32]=2)[C@@H:9]([C:13]2[CH:30]=[CH:29][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2[C:40]3[C:35](=[CH:36][C:37]([F:42])=[C:38]([F:41])[CH:39]=3)[N:34]=[CH:33][CH:32]=2)[C@@H:9]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:18])=[CH:29][CH:30]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58349495HCID 58349495, compound

Product 1

HCID 58349431HCID 58349431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the slower-eluting isomer of tert-butyl N-(4-{(1S)-1-[(4-chlorophenyl)(6,7-difluoroquinolin-4-yl)methyl]butyl}benzoyl)-β-alaninate from Step G (34 mg, 0.058 mmol) in CH2Cl2 (2.0 mL) was treated with TFA (1.0 mL). After stirring at room temperature overnight, the solution was concentrated. The residue was purified by preparative reverse phase HPLC, eluting with acetonitrile/water+0.1% formic acid. Following lyophilization, this afforded the title compound as a fluffy, white solid: 1H NMR (500 MHz, CDCl3): δ 8.95 (s, 1H); 8.10-8.01 (m, 2H); 7.85 (d, J=5.0 Hz, 1H); 7.53 (d, J=7.8 Hz, 2H); 7.38 (d, J=8.4 Hz, 2H); 7.34 (d, J=8.4 Hz, 2H); 7.21 (d, J=7.8 Hz, 2H); 6.97 (s, 1H); 4.93 (d, J=11.4 Hz, 1H); 3.65-3.54 (m, 3H); 2.56 (t, J=5.5 Hz, 2H); 1.65-1.53 (m, 2H); 1.13-0.97 (m, 2H); 0.75 (t, J=7.2 Hz, 3H); LC4: 2.26 min. (M+H) 537.

Workup

  1. concentrationthe solution was concentrated
  2. customThe residue was purified by preparative reverse phase HPLC
  3. washeluting with acetonitrile/water+0.1% formic acid

Sources & evidence

ORD record
ord-57a30531093147fea9a8ba28a31f98d1
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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