Trifluoroacetic acid → HCID 66716780, compound

HRID 1184492Notes

Reaction equation

HRID 1184492 reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[C:8]([CH2:26][CH2:27][CH3:28])=[CH:9][C:10]([CH2:12][N:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)=[CH:11][C:5]=2[NH:4][C:3]1=[O:29].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][CH:2]1[O:7][C:6]2[C:8]([CH2:26][CH2:27][CH3:28])=[CH:9][C:10]([CH2:12][N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[CH:11][C:5]=2[NH:4][C:3]1=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68069205HCID 68069205, compound

Product 1

HCID 66716780HCID 66716780, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

In a 20 mL scintillation vial was added tert-butyl 4-((2-methyl-3-oxo-8-propyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazine-1-carboxylate 358D (90 mg, 0.223 mmol) and TFA (2.0 mL, 26.0 mmol) in DCM (2.0 mL) and stirred at 23° C. for 1 h. The reaction was concentrated in vacuo, taken up in MeOH, and filtered through a PL-HCO3 MP resin column to give the free base. The MeOH filtrate was concentrated in vacuo to give the title compound as a yellow solid (68 mg, 0.224 mmol, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88 (t, J=7.33 Hz, 3H) 1.38 (d, J=6.82 Hz, 3H) 1.53 (dt, 2H) 2.43-2.49 (m, 4H) 2.52 (br. s., 2H) 3.00 (d, J=4.29 Hz, 4H) 3.33 (br. s., 1H) 3.39 (s, 2H) 4.60 (q, J=6.74 Hz, 1H) 6.63-6.76 (m, 2H) 10.58 (s, 1H). ESI-MS: m/z 304.3 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. filtrationfiltered through a PL-HCO3 MP resin column
  3. customto give the free base
  4. concentrationThe MeOH filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a6708b0a963643a8a0c72b1516ef74b8
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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