Triethylamine → HCID 11595114, compound

HRID 490085Notes

Reaction equation

HRID 490085 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[N:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:27](Cl)(=[O:31])[CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[N:17]=[CH:16][C:15]([CH2:18][NH:19][C:27](=[O:31])[CH2:28][CH2:29][CH3:30])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 62369742HCID 62369742, compound

Product 1

HCID 11595114HCID 11595114, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 26 mg (0.1 mmol) C-[6-(4-cyclopentyl-piperazin-1-yl)-pyridin-3-yl]-methylamine, 20 mg (0.2 mmol) triethylamine and 12 mg (0.11 mmol) butyryl chloride in DCM was stirred at room temperature. After evaporation acetonitrile/DMF was added and the mixture was 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 20.3 mg (61%) of the title compound. (m/e): 331.3

Workup

  1. customAfter evaporation acetonitrile/DMF
  2. additionwas added
  3. customthe mixture was subjected to preparative HPLC purification on reversed phase
  4. washeluting with a gradient of acetonitrile/water (0.05% triethylamine)
  5. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-23f5079a2cc443078a78b1a4b8aa46a5
Source dataset
uspto-grants-2009_05
Patent number
US07528135B2

Reaction notes

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