Trifluoroacetic acid → HCID 178480675, compound

HRID 1092032Notes

Reaction equation

HRID 1092032 reaction equation
[NH2:1][C:2]1[N:6](C(OC(C)(C)C)=O)[N:5]=[C:4]([CH2:14][CH2:15][C:16]2[CH:24]=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[CH:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.FC(F)(F)C(O)=O>N1C=CC=CC=1>[O:20]1[C:19]2[CH:23]=[CH:24][C:16]([CH2:15][CH2:14][C:4]3[CH:3]=[C:2]([NH:1][C:36](=[O:37])[C:35]4[CH:34]=[CH:33][C:32]([N:29]5[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]5)=[CH:40][CH:39]=4)[NH:6][N:5]=3)=[CH:17][C:18]=2[O:22][CH2:21]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 116300684-(4-methylpiperazin-1-yl)benzoyl ChlorideHCID 66590085Tert-butyl 5-amino-3-(2-benzo[1,3]dioxol-5-ylethyl)pyrazole-1-carboxylate

Product 1

HCID 178480675HCID 178480675, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl 5-amino-3-(2-benzo[1,3]dioxol-5-ylethyl)pyrazole-1-carboxylate (229 mg, 0.69 mmol, 1.0 eq) in pyridine (5 ml) at 5° C. was added 4-(4-methylpiperazin-1-yl)benzoyl chloride (181 mg, 0.76 mmol, 1.1 eq). The reaction mixture was stirred to 60° C. for 24 h. After this time, the mixture was concentrated and redissolved in DCM (10 ml). Trifluoroacetic acid (464 μl, 6.25 mmol, 8.25 eq) was added and the reaction mixture stirred for 2 h at 25° C. The reaction mixture was then concentrated. The crude product was purified by reverse-phase prep. HPLC (basic) using a 30-50% gradient of acetonitrile in water containing 1% ammonium hydroxide solution. The clean fractions were combined and evaporated to afford the title compound as a white solid. (12 mg, 4%); 1H NMR (300.132 MHz, DMSO) δ 2.28 (s, 3H), 2.49 (t, 2H), 2.89 (s, 2H), 3.31-3.37 (m, 8H), 6.01 (s, 2H), 6.43 (s, 1H), 6.74 (d, 1H), 6.86 (d, 2H), 7.01 (d, 2H), 7.94 (d, 2H), 10.36 (s, 1H), 12.11 (s, 1H); MS: m/z 434 (MH+).

Workup

  1. concentrationAfter this time, the mixture was concentrated
  2. dissolutionredissolved in DCM (10 ml)
  3. stirringthe reaction mixture stirred for 2 h at 25° C
  4. concentrationThe reaction mixture was then concentrated
  5. customThe crude product was purified by reverse-phase prep
  6. customevaporated

Sources & evidence

ORD record
ord-2e3aa5c14bd0413c86a8557e5b3eaf46
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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