Triethylamine → HCID 178464640, compound

HRID 1396054Notes

Reaction equation

HRID 1396054 reaction equation
[CH2:1]([NH:3][C:4]([N:19]1[CH2:23][CH:22]([CH2:24][CH3:25])[CH:21]=[N:20]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]=1Br)(=[O:8])=[O:7])[CH3:2].C(N(CC)CC)C>CCO>[CH2:1]([NH:3][C:4]([N:19]1[CH2:23][CH:22]([CH2:24][CH3:25])[CH:21]=[N:20]1)=[N:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:7])=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178464637HCID 178464637, compound

Product 1

HCID 178464640HCID 178464640, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.30 g 5-Bromo-2,3-dihydro-1H-indole-6-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide in 50 mL EtOH was added 0.94 mL of triethylamine. The mixture was degassed thoroughly, and 10 mol % of palladium on carbon was added. The mixture was hydrogenated overnight at a H2 pressure of 1 atm. The mixture was filtered over Hyflo, the Hyflo was washed with EtOH, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (DCM→DCM/EA 95:5→DCM/EA 9:1) to give 0.20 g (76%) of 2,3-Dihydro-1H-indole-6-sulfonic acid ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methyleneamide as a red oil. 1H NMR (400 MHz, CDCl3) δ 0.96 (t, J=7.52 Hz, 3H), 1.14 (t, J=7.22 Hz, 3H), 1.43-1.67 (m, 2H), 3.04 (t, J=8.43 Hz, 3H), 3.42-3.52 (m, 2H), 3.60 (t, J=8.43 Hz, 2H), 3.66 (dd, J=11.44, 7.83 Hz, 1H), 4.06 (t, J=11.29 Hz, 1H), 6.89 (d, J=1.50 Hz, 1H), 7.10-7.15 (m, 2H), 7.24-7.27 (m, 1H). [NH's invisible].

Workup

  1. customThe mixture was degassed thoroughly
  2. addition10 mol % of palladium on carbon was added
  3. filtrationThe mixture was filtered over Hyflo
  4. washthe Hyflo was washed with EtOH
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (DCM→DCM/EA 95:5→DCM/EA 9:1)

Sources & evidence

ORD record
ord-86c1f72e7ae844acb32b6e0f0be04a8c
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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