Piperidine → HCID 178492926, compound

HRID 2235476Notes

Reaction equation

HRID 2235476 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[NH2:11][C:12]1[NH:13][C:14]2[C:15]([N:36]=1)=[CH:16][C:17]1[C:18]([CH3:35])([CH3:34])[C:19](=[O:33])[N:20]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[O:31][CH3:32])[C:21]=1[CH:22]=2.CCN(C(C)C)C(C)C.N1CCCCC1>C1COCC1.CO>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:20]2[C:21]3[CH:22]=[C:14]4[NH:13][C:12]([NH:11][C:5](=[O:6])[C:4]5[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=5)=[N:36][C:15]4=[CH:16][C:17]=3[C:18]([CH3:35])([CH3:34])[C:19]2=[O:33])=[C:25]([O:31][CH3:32])[CH:26]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 743753-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 178492927HCID 178492927, compound

Product 1

HCID 178492926HCID 178492926, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-methyl-benzoyl chloride (62 mg) in THF (2 ml) is added D9 (35.4 mg) and DIPEA (30 μl). The reaction mixture is stirred at 50° C. for 12 h. Afterwards MeOH (1 ml) and piperidine (100 μl) are added. After shaking for 2 h the mixture is evaporated to dryness and purified by preparative RP-HPLC, eluted with MeCN/water to give the desired product (5 mg).

Workup

  1. stirringAfter shaking for 2 h the mixture
  2. customis evaporated to dryness
  3. custompurified by preparative RP-HPLC
  4. washeluted with MeCN/water

Sources & evidence

ORD record
ord-5ffa07da35134240bece083406156d5d
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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