Piperazin-2-one → HCID 59639550, compound

HRID 556655Notes

Reaction equation

HRID 556655 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C[Al](C)C.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N:20]1[C:25]2[N:26]=[C:27]([NH:38][CH2:39][C:40](OC)=[O:41])[N:28]=[C:29]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[CH3:37])[C:24]=2[CH:23]=[CH:22][C:21]1=[O:44]>>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N:20]1[C:25]2[N:26]=[C:27]([NH:38][CH2:39][C:40](=[O:41])[N:4]3[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]3)[N:28]=[C:29]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[CH3:37])[C:24]=2[CH:23]=[CH:22][C:21]1=[O:44]

Participants

4

Reactant 3

HCID 231360Piperazin-2-oneHCID 16682925TrimethylaluminumHCID 59639612HCID 59639612, compound

Product 1

HCID 59639550HCID 59639550, compoundYield 29%

Procedure

Following the general procedure outlined in Example 193, piperazine-2-one (165 mg, 1.65 mmol), trimethylaluminum (0.83 mL, 1.65 mmol) and the product of Example 190 (150 mg, 0.33 mmol) were reacted to give the crude material. Preparative HPLC, eluting with acetonitrile/H2O (10/90, v/v to 90/10, v/v, over 10 min), followed by recrystallization from dichloromethane and hexane, gave the desired product 50 mg (29%). LC-MS: 523.2 (MH+, m/z), 1.68 (Rt, min).

Workup

  1. customto give the crude material
  2. washPreparative HPLC, eluting with acetonitrile/H2O (10/90, v/v to 90/10
  3. customv/v, over 10 min), followed by recrystallization from dichloromethane and hexane

Sources & evidence

ORD record
ord-3855ae534d6e49d6b6bb4f6afb515525
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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