Trifluoroacetic acid → HCID 59000780, compound

HRID 1594024Notes

Reaction equation

HRID 1594024 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C:13]1[C:14]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[C:15]([CH2:41][CH2:42][CH3:43])[N:16]2[C:21]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][C:18]([N:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1)=[N:17]2)=[O:12])[CH3:9]>C(Cl)Cl>[CH2:8]([O:10][C:11]([C:13]1[C:14]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[C:15]([CH2:41][CH2:42][CH3:43])[N:16]2[C:21]=1[C:20]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:19][C:18]([N:28]1[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]1)=[N:17]2)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59000806HCID 59000806, compound

Product 1

HCID 59000780HCID 59000780, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of 2-(4-t-butoxycarbonyl-piperazin-1-yl)-4-phenyl-7-propyl-pyrrolo[1,2-b]pyridazine-5,6-dicarboxylic acid diethyl ester (101) (105 mg, 0.186 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred for 1 h at ambient temperature and concentrated. Purification by flash chromatography (silica gel, 10% methanol/CHCl3) provided the title compound. 1H NMR (DMSO-d6) δ 1.05-1.11 (m, 6H), 1.39 (t, 3H, J=7.2 Hz), 3.34 (t, 2H, J=7.4 Hz), 3.40-3.42 (m, 4H), 3.72 (q, 2H, J=7.0 Hz), 3.92-3.95 (m, 4H), 4.35 (q, 2H, J=7.1 Hz), 6.99 (s, 1H), 7.57-7.67 (m, 5H), 8.94 (brs, 2H). Mass Spectrum (ES+) m/e=465.1 (M+1-114 (CF3CO2H)).

Workup

  1. concentrationconcentrated
  2. customPurification by flash chromatography (silica gel, 10% methanol/CHCl3)

Sources & evidence

ORD record
ord-b558861748c14a1e9c8b8f54ad1ac8ff
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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