Pyridine → HCID 21100628, compound

HRID 1724826Notes

Reaction equation

HRID 1724826 reaction equation
[NH2:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:13]([N:15]3[CH2:20][CH2:19][CH:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH2:17][CH2:16]3)=[O:14])=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([C:29](=[O:35])[C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:3]1.N1C=CC=CC=1.[C:42](Cl)(=[O:44])[CH3:43]>C1COCC1>[C:42]([NH:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:13]([N:15]3[CH2:16][CH2:17][CH:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH2:19][CH2:20]3)=[O:14])=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([C:29](=[O:35])[C:30]([N:32]([CH3:33])[CH3:34])=[O:31])=[CH:3]1)(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 21100634HCID 21100634, compound

Product 1

HCID 21100628HCID 21100628, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of 2-{1-Amino-5-[4-(4-fluoro-benzyl)-piperidine-1-carbonyl]-6-methoxy-1H-indol-3-yl}-N,N-dimethyl-2-oxo-acetamide (100 mg, 0.21 mmol) in anhydrous THF (3 mL) was added pyridine (60 uL, 0.63 mmol) and acetyl chloride (45 uL, 0.63 mmol) at 0° C. The mixture became clear and was stirred continually at RT for 72 h. The reaction mixture was evaporated in vacuo. The crude material was added water and it was extracted with CH2Cl2. The organic extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by radial chromatography with 0-3% MeOH/CHCl3 to give 30 mg (28% ) of the desired product. M+H+ (523).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionThe crude material was added water and it
  3. extractionwas extracted with CH2Cl2
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by radial chromatography with 0-3% MeOH/CHCl3

Sources & evidence

ORD record
ord-62863f95a8314099be32b08782f4242d
Source dataset
uspto-grants-2009_02
Patent number
US07488744B2

Reaction notes

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