Water → HCID 58299856, compound

HRID 79187Notes

Reaction equation

HRID 79187 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH2:15])[N:13]=[CH:14][C:9]=3[C:8]3[CH:16]=[CH:17][N:18]=[C:19]([F:20])[C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.F[C:23](F)(F)[C:24]([OH:26])=O>C([O-])([O-])=O.[K+].[K+]>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:17]4[N:18]=[CH:19][C:7]([N:6]5[CH2:10][CH2:23][C:24](=[O:26])[CH2:2][CH2:1]5)=[CH:8][CH:16]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:16]=[CH:17][N:18]=[C:19]([F:20])[C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 582996889-Cyclopentyl-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 58299856HCID 58299856, compoundYield 170.8%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

Compound 245 (200 mg, 0.41 mmol) was dissolved in a solution of water (0.150 mL, 8.33 mmol) in trifluoroacetic acid (3.00 mL, 38.9 mmol). The solution was stirred at room temperature for 2 hours and then poured into aqueous K2CO3 (10%, 30 mL). This was extracted with dichloromethane+10% methanol (3×30 mL), and the combined organics were dried (MgSO4) and evaporated to give a yellow solid. Silica gel chromatography (gradient elution hexanes+2.5% TEA/50-100% ethyl acetate+2.5% TEA) afforded compound 305 as a yellow solid (156 mg, 86%).

Workup

  1. extractionThis was extracted with dichloromethane+10% methanol (3×30 mL)
  2. dry with materialthe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow solid
  5. washSilica gel chromatography (gradient elution hexanes+2.5% TEA/50-100% ethyl acetate+2.5% TEA)

Sources & evidence

ORD record
ord-c632f2d05f5c4419bf429657a69aab32
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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