Trifluoroacetic acid → Trifluoroacetic acid

HRID 2370627Notes

Reaction equation

HRID 2370627 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][N:33]2C(OC(C)(C)C)=O)=[CH:28][CH:27]=1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[CH:15]=[N:14][C:13]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]4)=[CH:30][CH:31]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 46835477Tert-butyl 2-(4-aminophenyl)piperidine-1-carboxylateHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 2

HCID 6422Trifluoroacetic acidHCID 601689796-(2-chlorophenyl)-2-{[4-(piperidin-2-yl)phenyl]amino}imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of Example 1E (0.048 g, 0.133 mmol) and tert-butyl 2-(4-aminophenyl)piperidine-1-carboxylate (0.059 g, 0.213 mmol) was heated in a capped vial at 120° C. for 1 hour. The reaction mixture was treated with ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was dissolved in CH2Cl2 (2 mL) and treated with trifluoroacetic acid (0.103 ml, 1.334 mmol). The mixture was stirred at 35° C. for 5 hours, concentrated, and purified by HPLC (see protocol in Example 1F) to provide the title compound as a trifluoroacetic acid salt. 1H NMR (500 MHz, CD3OD) δ 1.89-1.72 (m, 2H), 2.16-1.96 (m, 4H), 3.25-3.16 (m, 1H), 3.51-3.43 (m, 1H), 4.29-4.22 (m, 1H), 7.08 (d, J=1.9 Hz, 1H), 7.62-7.50 (m, 5H), 7.72-7.66 (m, 1H), 7.97-7.86 (m, 3H), 9.19 (s, 1H). MS (ESI+) m/z 472.2 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2 (2 mL)
  6. concentrationconcentrated
  7. custompurified by HPLC (see protocol in Example 1F)

Sources & evidence

ORD record
ord-b33bd7c74b014fc09c7b84538f02bd46
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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