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Trifluoroacetic acid → HCID 118390074, compound

HRID 1478082
Notes
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Reaction equation

HRID 1478082 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.Cl.[CH3:26][N:27]1[C:31]([CH3:32])=[C:30]([NH2:33])[CH:29]=[N:28]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:10][CH:11]3[CH2:15][NH:14][CH2:13][CH:12]3[CH2:23]2)=[N:7][C:2]([NH:33][C:30]2[CH:29]=[N:28][N:27]([CH3:26])[C:31]=2[CH3:32])=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 467370451,5-Dimethyl-1H-pyrazol-4-amine--hydrogen chloride (1/1)HCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 118390074HCID 118390074, compoundYield 19.6%

Reagents, catalysts & solvents

1
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (579.1 mg, 1.55 mmol) and 1,5-dimethylpyrazol-4-amine hydrochloride (446.8 mg, 3.03 mmol) in dioxane (10 mL) was added trifluoroacetic acid (862.8 mg, 7.57 mmol). The reaction mixture was stirred at 100° C. overnight and adjusted to pH=10 with a saturated Na2CO3 solution, then extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM=1/10) to give the title compound as a beige solid (105.6 mg, 19.6%).

Workup

  1. extractionextracted with DCM (100 mL×3)
  2. washThe combined organic phases were washed with brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (MeOH/DCM=1/10)

Sources & evidence

ORD record
ord-767b7654f6524f418ade583e8ff9ae35
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09403801B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes