Trifluoroacetic acid → HCID 71726887, compound

HRID 870953Notes

Reaction equation

HRID 870953 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]2[O:23][CH:24]([C:31]([F:34])([F:33])[F:32])[C:25]3[C:30]([C:4]=2[CH:3]=1)=[CH:29][CH:28]=[N:27][CH:26]=3.C(O)(C(F)(F)F)=O>ClCCl>[Br:1][C:2]1[C:7]([O:8][CH2:9][C@@H:10]([NH2:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]2[O:23][CH:24]([C:31]([F:33])([F:34])[F:32])[C:25]3[C:30]([C:4]=2[CH:3]=1)=[CH:29][CH:28]=[N:27][CH:26]=3

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724442HCID 86724442, compound

Product 1

HCID 71726887HCID 71726887, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl ((2S)-1-((9-bromo-5-(trifluoromethyl)-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (50 mg, 0.092 mmol) in dichloromethane (10 mL) at room temperature was added TFA (0.035 mL, 0.458 mmol) and stirred overnight. The solvent was removed under reduced pressure to afford a residue which was purified by preparative HPLC using 0.1% TFA in MeOH. The purification afforded (2S)-1-((9-bromo-5-(trifluoromethyl)-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-amine (15 mg, 0.033 mmol, 36% yield) as a yellow solid. 1H NMR (400 MHz, MeOD) δ 8.64 (m, 1H), 8.54 (m, 1H), 8.23 (m, 1H), 7.88 (s, 1H), 6.91 (s, 1H), 6.10 (m, 1H), 4.3 (m, 1H), 4.12 (m, 1H), 3.52 (m, 1H), 1.85 (m, 1H), 1.72-1.69 (m, 1H), 1.61-1.56 (m, 1H), 1.05 (m, 6H). LCMS (ESI) m/e 445.2 [(M+H)+, calcd for C19H21BrF3N2O2 445.1]; LC/MS retention time (Method C): tR=1.74 min; HPLC retention time (method A): tR=5.66 min, 5.75 min (diastereomeric mixture); HPLC retention time (method B): tR=6.27 min, 6.34 min (diastereomeric mixture).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford a residue which
  3. customwas purified by preparative HPLC
  4. customThe purification

Sources & evidence

ORD record
ord-e0ad2bf992c4405485d022a58e1425e5
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

Loading…