Isopropylamine → HCID 16071255, compound

HRID 2240027Notes

Reaction equation

HRID 2240027 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:8][CH:9]=2)[C:4]([S:25]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[N:3]1.[CH:38]([NH2:41])([CH3:40])[CH3:39]>C1COCC1>[CH:38]([NH:41][CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[N:3]=[C:4]2[S:25]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:26])=[O:27])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 6363Isopropylamine2×HCID 58812060HCID 58812060, compound

Product 1

HCID 16071255HCID 16071255, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of toluene-4-sulfonic acid 2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethyl ester (0.433 g, 0.807 mmol) and isopropylamine (1.0 mL, 12 mmol) in THF (10 mL) was stirred at 80° C. in a sealed tube for 15 hours. Additional isopropylamine (1.0 mL, 12 mmol) was added, and the reaction mixture was stirred at 80° C. for 21 hours. It was allowed to cool to room temperature, and partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 0.25% ammonium hydroxide/2.5% methanol in chloroform. Drying at 63° C. in vacuo for 30 minutes yielded isopropyl-{2-[1-methyl-3-(naphthalene-1-sulfonyl)-1H-indazol -5-yloxy]-ethyl}-amine as a yellow semi-solid 0.198 g, 57.9%). This was dissolved in chloroform, and ethereal hydrochloride was added. The precipitate was filtered and dried at 85° C. in vacuo for 13 hours to give the hydrochloride as an off-white solid (0.180 g): MP: 274-6° C. (dec).; Mass Spectrum (+EI, [M+H]+) m/z 424.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned in ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialIt was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. customDrying at 63° C. in vacuo for 30 minutes

Sources & evidence

ORD record
ord-023811b499c24f3f948da9679a111389
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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