Trifluoroacetic acid → HCID 53390240, compound

HRID 1045753Notes

Reaction equation

HRID 1045753 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[N:16]([CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:11]1([C:14]2[C:15]3[N:16]([CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58447048HCID 58447048, compound

Product 1

HCID 53390240HCID 53390240, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A 25 mL round bottom flask was charged with ethyl 8-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-(thiophen-2-yl)imidazo[1,2-a]pyrazine-2-carboxylate (1.13 g, 2.47 mmol), trifluoroacetic acid (5 mL) and CH2Cl2 (10 mL). The mixture was stirred at 25° C. for 1 h. Reaction progress was monitored by LC-MS. Work-up: the solvent was evaporated. The residue was mixed with saturated aqueous NaHCO3 and extracted with EtOAc (30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with a 1:20 MeOH/CH2Cl2, to afford 0.75 g (84%) of the product. 1H NMR (300 MHz, CD3OD) δ: 8.40 (s, 1H), 7.69 (dd, J=5.1, 1.2 Hz, 1H), 7.58 (s, 1H), 7.52 (dd, J=3.9, 1.2 Hz, 1H), 7.28 (dd, J=5.1, 3.9 Hz, 1H), 4.54 (t, J=5.1 Hz, 4H), 4.41 (q, J=7.2 Hz, 2H), 3.39 (t, J=5.1 Hz, 4H), 1.38 (t, J=7.2 Hz, 3H). MS m/z: 358 (M+H+).

Workup

  1. customReaction progress
  2. customthe solvent was evaporated
  3. additionThe residue was mixed with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc (30 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with a 1:20 MeOH/CH2Cl2

Sources & evidence

ORD record
ord-47372b4870e245c6a99ba629d37a136e
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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