Hydrochloric Acid → HCID 178464639, compound

HRID 1396047Notes

Reaction equation

HRID 1396047 reaction equation
[CH2:1]([NH:3][C:4]([N:21]1[CH2:25][CH:24]([CH2:26][CH3:27])[CH:23]=[N:22]1)=[N:5][S:6]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](C(=O)C)[CH2:13][CH2:12]2)(=[O:8])=[O:7])[CH3:2].Cl.C([O-])(O)=O.[Na+]>CCO>[CH2:1]([NH:3][C:4]([N:21]1[CH2:25][CH:24]([CH2:26][CH3:27])[CH:23]=[N:22]1)=[N:5][S:6]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2)(=[O:7])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178464638HCID 178464638, compound

Product 1

HCID 178464639HCID 178464639, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.74 g 1-acetyl-2,3-dihydro-1H-indole-5-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide was dissolved in 100 mL EtOH, and 22.2 mL of 1M HCl was added. The mixture was stirred for 5 h. under reflux. After cooling to room temperature, the mixture was basified with a 5% NaHCO3 solution and extracted twice with DCM. The combined organic layers were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM→DCM/EA 4:1) to give 0.66 g (43%) of 2,3-Dihydro-1H-indole-5-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 0.97 (t, J=7.52 Hz, 3H), 1.15 (t, J=7.22 Hz, 3H), 1.44-1.68 (m, 2H), 2.97-3.13 (m, 3H), 3.42-3.54 (m, 2H), 3.58-3.72 (m, 3H), 3.99-4.09 (m, 1H), 6.55 (d, J=8.13 Hz, 1H), 6.88 (d, J=1.50 Hz, 1H), 7.00 (br.s., 1H), 7.55-7.65 (m, 2H) [NH invisible].

Workup

  1. temperatureunder reflux
  2. extractionextracted twice with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography (DCM→DCM/EA 4:1)

Sources & evidence

ORD record
ord-e8caa31068d74711a2d36e6ca9e54eb1
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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