Cyclopropylamine → HCID 178527283, compound

HRID 2240009Notes

Reaction equation

HRID 2240009 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH2:26]OS(C4C=CC(C)=CC=4)(=O)=O)[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:38]1([NH2:41])[CH2:40][CH2:39]1>C1COCC1>[CH:38]1([NH:41][CH2:26][CH2:25][CH2:24][O:23][C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[S:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:12])=[O:13])[CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 178427737HCID 178427737, compound

Product 1

HCID 178527283HCID 178527283, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of toluene-4-sulfonic acid 3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl ester (0.080 mg, 0.15 mmol) and cyclopropylamine (0.45-0.75 mmol) in THF (10 mL) was stirred at 90° C. for about 2 hours in a sealed tube. After cooling to ambient temperature the reaction mixture was solvent evaporated. It was dissolved in ethyl acetate and washed twice with aqueous sodium bicarbonate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified twice by flash chromatography using 0.75% ammonium hydroxide/7.5% methanol in chloroform and 0.5% ammonium hydroxide/5.0% methanol in chloroform to give cyclopropyl-{3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl}-amine as a clear yellow film (51.0 mg, 80.7%). This compound was dissolved in methanol, and ethereal hydrochloride was added. Concentrating and drying in vacuo for 24 hours at 83° C. gave the hydrochloride as a yellow foam (48.9 mg, 71.2%); Mass Spectrum (+EI, [M+H]+) m/z 422. 1HNMR (500 MHz, DMSO-d6): δ14.15 (s, 1H), 9.01 (s, 2H), 8.74-8.76 (m, 1H), 8.51-8.53 (m, 1H), 8.27 (d, 1H, J=8.29 Hz), 8.02-8.05 (m, 1H), 7.71-7.75 (m, 1H), 7.51-7.65 (m, 3H), 7.29 (d, 1H, J=2.19 Hz), 7.08-7.11 (m, 1H), 4.11 (t, 2H, J=6.10 Hz), 3.11-3.20 (br, s, 2H), 2.65-2.75 (m, 1H), 2.08-2.15 (m, 2H), 0.83-0.87 (m, 2H), 0.70-0.77 ppm (m, 2H). Elemental Analysis for C23H23N3O3S.1.00 mol HCl.0.70 mol H2O: Calcd: C, 58.70; H, 5.44; N, 8.93; Found: C, 58.70; H, 5.09; N, 8.68.

Workup

  1. customevaporated
  2. dissolutionIt was dissolved in ethyl acetate
  3. washwashed twice with aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified twice by flash chromatography

Sources & evidence

ORD record
ord-1a082926219b413aa214924ee30f665a
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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