Trifluoroacetic acid → HCID 11948176, compound

HRID 1806525Notes

Reaction equation

HRID 1806525 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:47])=[C:12]([C:14]3[C:15]4[CH:37]=[CH:36][C:35](=[O:38])[N:34]([C:39]5[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=5[F:46])[C:16]=4[N:17]=[C:18]([NH:20][CH:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[N:19]=3)[CH:13]=2)=[O:7])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C1COCC1>[CH:1]1([CH2:4][NH:5][C:6](=[O:7])[C:8]2[CH:9]=[CH:10][C:11]([CH3:47])=[C:12]([C:14]3[C:15]4[CH:37]=[CH:36][C:35](=[O:38])[N:34]([C:39]5[C:40]([F:46])=[CH:41][CH:42]=[CH:43][C:44]=5[F:45])[C:16]=4[N:17]=[C:18]([NH:20][CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[N:19]=3)[CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59212723HCID 59212723, compound

Product 1

HCID 11948176HCID 11948176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-{[4-(5-{[(cyclopropylmethyl)-amino]carbonyl}-2-methylphenyl)-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}-1-piperidinecarboxylate in THF (2 mL) was added TFA (3.0 mL). The reaction mixture was stirred for about 12 h and concentrated. The residue was mixed with H2O (5.0 mL) and EtOAc (20.0 mL) and the resultant mixture was basified with 2.5 N NaOH aqueous (hereinafter “aq”) solution. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organic phases were washed with saturated aq. NaCl, dried over Na2SO4, filtered, and concentrated. Purification via a CombiFlash system (DCM:MeOH=10:1) then afforded the title compound: LC-MS m/z 545 (M+H)+, 1.65 min (ret. time).

Workup

  1. concentrationconcentrated
  2. additionThe residue was mixed with H2O (5.0 mL) and EtOAc (20.0 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  5. washThe combined organic phases were washed with saturated aq. NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification via a CombiFlash system (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-a8effcfe233f47ba9ffffb274b68f693
Source dataset
uspto-grants-2013_01
Patent number
US08354416B2

Reaction notes

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