Hydrochloric Acid → HCID 23004033, compound

HRID 396355Notes

Reaction equation

HRID 396355 reaction equation
[CH2:1]([N:8](C(OC(C)(C)C)=O)[CH2:9][CH:10]([O:29][CH3:30])[C:11]1[C:20]2[C:15](=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([C:25]([F:28])([F:27])[F:26])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:38]>O1CCOCC1>[ClH:38].[CH2:1]([NH:8][CH2:9][CH:10]([O:29][CH3:30])[C:11]1[C:20]2[C:15](=[C:16]([C:21]([F:22])([F:23])[F:24])[CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([C:25]([F:28])([F:27])[F:26])[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23004019HCID 23004019, compound

Product 1

HCID 23004033HCID 23004033, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To N-Benzyl-N-tert-butoxycarbonyl-β-methoxy-2,8-bis(trifluoromethyl)-4-quinolineethanamine (113 mg, 0.21 mmol) in dioxan (1 mL) was added HCl (4-M in dioxan, 0.25 mL, 1 mmol) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo, triturated with ether and filtered to give the title compound (54 mg, 60%) as a white solid: mp 232-233° C.; NMR δH (400 MHz, DMSO-d6) 3.17-3.41 (2H, m), 3.34 (3H, s), 4.19 (1H, d, J 13.8 Hz), 4.22 (1H, d, J 13.8 Hz), 5.78 (1H, dd, J 9.26, 2.1 Hz), 7.36-7.46 (3H, m), 7.53-7.62 (2H, m), 8.00 (1H, t, J 8.0 Hz), 8.03 (1H, s), 8.42 (1H, d, J 7.7 Hz), 8.80 (1H, d, J 8.62 Hz); Anal. Calcd for C21H18F6N2O.HCl: C, 54.26; H, 4.12; N, 6.02. Found C, 54.04; H, 4.30; N, 5.79.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customtriturated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-65b9c1f38afa4001be6b070203ef8571
Source dataset
uspto-grants-2003_08
Patent number
US06608085B1

Reaction notes

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