Water → HCID 67269311, compound

HRID 600217Notes

Reaction equation

HRID 600217 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[N:17]=[C:16]([NH2:18])[CH:15]=[CH:14][N:13]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:19]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1.CC(C)([O-])C.[K+].O>C1COCC1.CO>[CH:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]3[N:17]=[C:16]([NH:18][C:24]([CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[O:25])[CH:15]=[CH:14][N:13]=3)[CH2:10][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 78284Cyclopentanecarbonyl chlorideHCID 23665647Potassium tert-butoxideHCID 42631890HCID 42631890, compound

Product 1

HCID 67269311HCID 67269311, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10 mg (0.04 mmol) 2-(4-cyclopentyl-piperazin-1-yl)-pyrimidin-4-ylamine, 10.8 mg (0.082 mmol) cyclopentylcarbonyl chloride and 13.5 mg (0.12 mmol) potassium t-butoxide in 0.7 mL THF was shaken at room temperature for 16 h. The mixture was treated with water and methanol and subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 3 mg (21%) of the title compound as white solid. MS (m/e): 344.1 (MH+).

Workup

  1. customsubjected to preparative HPLC purification on reversed phase
  2. washeluting with a gradient of acetonitrile/water (0.05% triethylamine)
  3. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-741116869fac40e5bdbeaff8a6a49ce4
Source dataset
uspto-grants-2011_03
Patent number
US07902184B2

Reaction notes

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