Acetic Anhydride → N-{[(1S,2S)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639856Notes

Reaction equation

HRID 1639856 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C@H:13]2[CH2:15][C@@H:14]2[CH2:16][NH2:17])=[N:5]1.C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>O1CCCC1>[CH3:3][N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C@H:13]2[CH2:15][C@@H:14]2[CH2:16][NH:17][C:25](=[O:27])[CH3:26])=[N:5]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 667205841-[(1S,2S)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride

Product 1

HCID 59334474N-{[(1S,2S)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(1S,2S)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride (300 mg, 1.09 mmol) and triethylamine (305 μL, 2.19 mmol) in tetrahydrofuran (10 mL) was added acetic anhydride (124 μL, 1.31 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=5/95→20/80) to give the title compound (242 mg, yield 99%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=5/95→20/80)

Sources & evidence

ORD record
ord-87b5f620265246f1aaa4085193749bf2
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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