Pyridine → HCID 67619373, compound

HRID 2399551Notes

Reaction equation

HRID 2399551 reaction equation
Cl.[NH2:2][C@H:3]1[C@@H:7]([CH3:8])[CH2:6][N:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:20])[N:12]=2)=[O:10])[CH2:4]1.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>O>[C:27]([NH:2][C@H:3]1[C@@H:7]([CH3:8])[CH2:6][N:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:20])[N:12]=2)=[O:10])[CH2:4]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67619063HCID 67619063, compound

Product 1

HCID 67619373HCID 67619373, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 mg (0.68 mmol) of cis-3-amino-4-methyl-1-(1-methylindazol-3-ylcarbonyl)pyrrolidine hydrochloride was added 0.7 ml of pyridine, and 0.07 ml (0.75 mmol) of acetic anhydride was added dropwise under ice cooling. Then, after heated to room temperature, the mixture was stirred overnight. To the reaction mixture was added water, and then the solution was extracted with methylene chloride. After washed with saturated saline solution and dried over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure to obtain crude oil. This was subjected to silica gel column chromatographic purification (methylene chloride:acetone=10:1) to obtain 176 mg (86.3%) of aimed compound. m.p. 202°-204° C.

Workup

  1. additionwas added dropwise under ice cooling
  2. extractionthe solution was extracted with methylene chloride
  3. washAfter washed with saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthe solution was concentrated under reduced pressure
  6. customto obtain crude oil
  7. customThis was subjected to silica gel column chromatographic purification (methylene chloride:acetone=10:1)

Sources & evidence

ORD record
ord-af5149e5e45a4c3e8368f808f65c084c
Source dataset
uspto-grants-1995_09
Patent number
US05449787

Reaction notes

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