Ethanolamine → 4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-{1-[2-(2-hydroxy-ethylamino)-pyrimidin-4-yl]-piperidin-4-ylmethyl}-piperazin-2-one

HRID 1433093Notes

Reaction equation

HRID 1433093 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:25][CH2:24][N:23]([C:26]5[CH:31]=[CH:30][N:29]=[C:28](Cl)[N:27]=5)[CH2:22][CH2:21]4)[C:15](=[O:33])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:34]=1.[CH2:35]([CH2:37][NH2:38])[OH:36]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]4[CH2:21][CH2:22][N:23]([C:26]5[CH:31]=[CH:30][N:29]=[C:28]([NH:38][CH2:37][CH2:35][OH:36])[N:27]=5)[CH2:24][CH2:25]4)[C:15](=[O:33])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:34]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 98073084-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one

Product 1

HCID 670138584-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-{1-[2-(2-hydroxy-ethylamino)-pyrimidin-4-yl]-piperidin-4-ylmethyl}-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one (0.40 g, 0.74 mmol) in EtOH is added ethanolamine (0.089 mL, 1.5 mmol). The solution is heated to reflux for 18 h and evaporated to dryness. The residue is chromatographed eluting successively with 1%, 2% and 4% MeOH in CH2Cl2. Fractions containing only product are combined and the solvent evaporated. Trituration with ether afforded the title compound as a yellow solid: MS (ESI): m/z 565 (M++H).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 18 h
  3. customevaporated to dryness
  4. customThe residue is chromatographed
  5. washeluting successively with 1%, 2% and 4% MeOH in CH2Cl2
  6. additionFractions containing only product
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-9b2b5a9323014e1ba0b15686aa0b7cfb
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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