Water → HCID 118158016, compound

HRID 2200896Notes

Reaction equation

HRID 2200896 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:12]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([Cl:30])[CH:23]=2)=[N:13][C:14](S(C)=O)=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[O:41]=[C:42]1[CH2:48][CH:47]2[NH:49][CH:44]([CH2:45][CH2:46]2)[CH2:43]1.O>C(Cl)Cl.C1COCC1.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[C:12]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([Cl:30])[CH:23]=2)=[N:13][C:14]([N:49]2[CH:44]3[CH2:45][CH2:46][CH:47]2[CH2:48][C:42](=[O:41])[CH2:43]3)=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochlorideHCID 118157494N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-formamide

Product 1

HCID 118158016HCID 118158016, compoundYield 19.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In DCM were dissolved N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methyl sulfinyl)pyrimidine-5-formamide (222 mg, 0.5 mmol) and DIEA (0.25 mL, 1.35 mmol). 3-oxo-8-azabicyclo[3.2.1] octane hydrochloride salt (90 mg, 0.6 mmol) was dissolved in THF and added to the reaction mixture at 0° C. The reaction was conducted at ambient temperature, followed by addition of water and extraction with ethyl acetate. The organic phase was washed sequentially with water and brine, and dried over sodium sulfate. The solvent was removed by rotary evaporation. Purification was performed by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to give a white solid (50 mg, 19% yield).

Workup

  1. additionadded to the reaction mixture at 0° C
  2. customwas conducted at ambient temperature
  3. washThe organic phase was washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed by rotary evaporation
  6. customPurification

Sources & evidence

ORD record
ord-8bb4970c3aa94f46a7d4c2edc5f6fc0a
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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