Hydrochloric Acid → HCID 178464637, compound

HRID 2273968Notes

Reaction equation

HRID 2273968 reaction equation
[CH2:1]([NH:3][C:4]([N:22]1[CH2:26][CH:25]([CH2:27][CH3:28])[CH:24]=[N:23]1)=[N:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][N:15]2C(=O)C)=[CH:11][C:10]=1[Br:21])(=[O:8])=[O:7])[CH3:2].Cl.C([O-])(O)=O.[Na+]>CO>[CH2:1]([NH:3][C:4]([N:22]1[CH2:26][CH:25]([CH2:27][CH3:28])[CH:24]=[N:23]1)=[N:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][NH:15]2)=[CH:11][C:10]=1[Br:21])(=[O:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178464636HCID 178464636, compound

Product 1

HCID 178464637HCID 178464637, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.65 g 1-Acetyl-5-bromo-2,3-dihydro-1H-indole-6-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide was dissolved in 20 mL MeOH and 20.7 mL of 1M HCl in MeOH was added. The mixture was stirred overnight 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/EA 9:1→8:2) to give 0.35 g (64%) of 5-Bromo-2,3-dihydro-1H-indole-6-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 0.96 (t, J=7.37 Hz, 3H), 1.17 (t, J=7.22 Hz, 3H), 1.45-1.68 (m, 2H), 3.00-3.15 (m, 3H), 3.48-3.57 (m, 2H), 3.62 (t, J=8.43 Hz, 2H), 3.71 (dd, J=11.14, 7.52 Hz, 1H), 3.91 (br.s., 1H), 4.08-4.17 (m, 1H), 6.76 (br.s., 1H), 6.90 (d, J=1.50 Hz, 1H), 7.34 (s, 1H), 7.46 (s, 1H).

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/EA 9:1→8:2)

Sources & evidence

ORD record
ord-d6d85062119f4e139b780fcc02a6456f
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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