Trifluoroacetic acid → 5-{8-[4-(2-Oxo-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-2,3-dihydro-isoindol-1-one

HRID 605976Notes

Reaction equation

HRID 605976 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[C:22]4[N:23]([N:37]=[CH:38][N:39]=4)[C:24]([C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[C:32](=[O:36])[NH:31][CH2:30]5)=[CH:25][N:26]=3)=[CH:16][CH:15]=2)[C:10](=[O:40])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[O:40]=[C:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]2[C:22]3[N:23]([N:37]=[CH:38][N:39]=3)[C:24]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[C:32](=[O:36])[NH:31][CH2:30]4)=[CH:25][N:26]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670475993-Oxo-4-{4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 248897885-{8-[4-(2-Oxo-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-2,3-dihydro-isoindol-1-oneYield 86.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-oxo-4-{4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (59 mg, 0.1 mmol) in 3:1 DCM:TFA (1.2 mL) is stirred at room temperature for 1 hour. The reaction mixture is diluted with DCM and basified with sat. NaHCO3. The aqueous layer is extracted with DCM (3×) and the organic layers are combined, dried over MgSO4, filtered and concentrated under vacuum to afford the title compound as a yellow solid (38 mg, 86%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 3.07 (2H, m), 3.44 (2H, s), 3.64 (2H, m), 4.50 (2H, s), 7.32 (2H, d), 7.83 (1H, d), 8.04-8.10 (4H, m), 8.22 (1H, s), 8.70 (1H, br s), 8.74 (1H, s), 10.25 (1H, s). LCMS: Rt 7.17 min (93.7%), m/z (APCI) 441 (M+H)+.

Workup

  1. extractionThe aqueous layer is extracted with DCM (3×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-885f3997cfa1464a86c05ca4c0c42676
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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