Water → HCID 86749007, compound

HRID 2400053Notes

Reaction equation

HRID 2400053 reaction equation
[C:1]([CH2:4][C:5]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[O:6])([OH:3])=O.Cl.C(N=C=N[CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])C.[N:30]1([C:35]2[N:40]=[C:39](N3CCNCC3)[CH:38]=[C:37]([N:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)[N:36]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1.[OH2:52]>C(#N)C>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([S:8]([NH:7][C:5]([CH2:4][C:1]([N:36]2[CH2:37][CH2:38][CH2:24][CH:25]2[C:26]([N:27]2[CH2:28][CH2:34][N:30]([C:35]3([N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[N:40]=[CH:39][CH:38]=[C:37]([N:47]4[CH2:48][CH2:49][CH2:50][CH2:51]4)[NH:36]3)[CH2:31][CH2:29]2)=[O:52])=[O:3])=[O:6])(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 15470414HCID 15470414, compound

Product 1

HCID 86749007HCID 86749007, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1 g of N-(carboxymethylcarbonyl)paratoluenesulphonamide in 30 ml of acetonitrile is added, at room temperature and under stirring, with 0.97 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1.56 g of (-)-N'-[pyrrolidin-2-yl)carbonyl]-N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-4-yl]piperazine, in this succession. After 3 hours the reaction mixture is added with 70 ml of water and extracted with ethyl acetate (3×20 ml). The combined organic extracts are washed with water (3×10 ml), dried over sodium sulfate and solvent is evaporated off under reduced pressure. The residue (1.5 g) is purified by silica gel chromatography (eluent 9.5:0.5 AcOEt/MeOH), to obtain 0.95 g of (-)-N'-[(1-(paratoluenesulphonamidocarbonyl-methylcarbonyl)pyrrolidin-2-yl)carbonyl]-N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-2-yl]piperazine, m.p. 170° C., [α]D =-26.9° (c=2.06 in EtOH).

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washThe combined organic extracts are washed with water (3×10 ml)
  3. dry with materialdried over sodium sulfate and solvent
  4. customis evaporated off under reduced pressure
  5. customThe residue (1.5 g) is purified by silica gel chromatography (eluent 9.5:0.5 AcOEt/MeOH)

Sources & evidence

ORD record
ord-7bceb7c3cf7e4797a40699efeebb2666
Source dataset
uspto-grants-1995_09
Patent number
US05453423

Reaction notes

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