Trifluoroacetic acid → 6-(4-Chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-5-piperidin-4-yl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204379Notes

Reaction equation

HRID 2204379 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:28](=[O:29])[C:27]3[CH:26]=[C:25]([C:30]4[C:31]([O:38][CH3:39])=[N:32][C:33]([O:36][CH3:37])=[N:34][CH:35]=4)[N:24]([CH:40]([CH3:42])[CH3:41])[C:23]=3[CH:22]2[C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[Cl:49][C:46]1[CH:47]=[CH:48][C:43]([CH:22]2[C:23]3[N:24]([CH:40]([CH3:42])[CH3:41])[C:25]([C:30]4[C:31]([O:38][CH3:39])=[N:32][C:33]([O:36][CH3:37])=[N:34][CH:35]=4)=[CH:26][C:27]=3[C:28](=[O:29])[N:21]2[CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703185HCID 86703185, compound

Product 1

HCID 867031846-(4-Chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-5-piperidin-4-yl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (32.4 mmol) was added to a solution of 4-[6-(4-chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-4-oxo-4,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (Step I06.1) (0.755 mmol) in CH2Cl2 (4 mL) at 0° C. After 1 h, the reaction mixture was quenched with a saturated aqueous solution of NaHCO3 and diluted with EtOAc, THF and NaCl. The separated aqueous phase was extracted with EtOAc/THF (2×). The combined organic phases were dried (MgSO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid (TFA-salt). tR: 4.34 min (HPLC 4); ESI-MS: tR=0.82 min, [M+H]+ 496/498(LC-MS 1).

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous solution of NaHCO3
  2. additiondiluted with EtOAc, THF and NaCl
  3. extractionThe separated aqueous phase was extracted with EtOAc/THF (2×)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-a311b88d006e46b284a9ff85b5d960c3
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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