Trifluoroacetic acid → HCID 86677327, compound

HRID 1842682Notes

Reaction equation

HRID 1842682 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[C:6]([N+:16]([O-:18])=[O:17])=[CH:5][C:4]=1[NH:19]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[C:6]([N+:16]([O-:18])=[O:17])=[CH:5][C:4]=1[NH2:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86677328HCID 86677328, compound2×

Product 1

HCID 86677327HCID 86677327, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-[2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl]carbamate (Intermediate 15, 1.4 g, 3.82 mmol) was dissolved in CH2Cl2 (20 mL) and TFA (5 mL) was then added. The mixture was stirred for 2 h at r.t. and was then concentrated in vacuo. The resulting residue was dissolved in CH3OH, absorbed onto an SCX column, washed with CH3OH and eluted with methanolic ammonia. The fractions that contained product were combined and concentrated. Purification by FCC, eluting with 1.5% 7N methanolic ammonia in CH2Cl2 gave the title compound (0.6 g, 59%) as an orange oil which crystallised on standing; 1H NMR: 2.22 (3H, s), 2.39-2.47 (4H, m), 2.87-2.97 (4H, m), 3.88 (3H, s), 4.99 (2H, s), 6.72 (1H, s), 7.20 (1H, s); m/z: ES+ MH+ 267.5.

Workup

  1. concentrationwas then concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in CH3OH
  3. customabsorbed onto an SCX column
  4. washwashed with CH3OH
  5. washeluted with methanolic ammonia
  6. concentrationconcentrated
  7. customPurification by FCC
  8. washeluting with 1.5% 7N methanolic ammonia in CH2Cl2

Sources & evidence

ORD record
ord-fe77b3c8edb7459db50e2fa925787edb
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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