Trifluoroacetic acid → 2-(8-Methoxy-1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine

HRID 540124Notes

Reaction equation

HRID 540124 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]2[CH2:7][N:8]([C:14]3[CH:23]=[C:22]([NH:24]C(=O)OC(C)(C)C)[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH3:32])[CH:20]=4)[N:15]=3)[CH2:9][CH2:10][S:11](=[O:13])(=[O:12])[C:5]=2[CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]2[CH2:7][N:8]([C:14]3[CH:23]=[C:22]([NH2:24])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([CH3:32])[CH:20]=4)[N:15]=3)[CH2:9][CH2:10][S:11](=[O:13])(=[O:12])[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71262340tert-Butyl [2-(8-Methoxy-1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]carbamate

Product 1

HCID 712621092-(8-Methoxy-1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amineYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture solution of tert-butyl [2-(8-methoxy-1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]carbamate (59.0 mg, 0.12 mmol) and trifluoroacetic acid (0.5 mL) in dichloromethane (2.0 mL) was stirred at room temperature for 6 hours. Then the reaction mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by preparative HPLC to afford 10.2 mg of the product as a white solid (yield was 21.5%). MS obsd. (ESI+) [(M+H)+] 384, 1H NMR (400 MHz, CD3OD) δ ppm 7.72 (d, J=8.34 Hz, 1 H), 7.58 (s, 1 H), 7.50 (d, J=2.78 Hz, 1 H), 7.43 (d, J=8.34 Hz, 1 H), 7.29 (dd, J=8.46, 1.89 Hz, 1 H), 7.12 (dd, J=8.34, 2.78 Hz, 1 H), 6.27 (s, 1 H), 5.02 (s, 2 H), 4.47 (brs, 2 H), 3.82 (s, 3 H), 3.56 (t, J=4.80 Hz, 2 H), 2.42 (s, 3 H).

Workup

  1. extractionThen the reaction mixture was extracted with ethyl acetate (100 mL)
  2. washThe organic layer was washed with brine (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-69ed86678950466193c24941556bfdb5
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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