Triethylamine → HCID 44219345, compound

HRID 1928829Notes

Reaction equation

HRID 1928829 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:22]([NH:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[O:23])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:38][S:39]([CH:42]=[CH2:43])(=[O:41])=[O:40].C(OCC)(=O)C>O1CCCC1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:22]([NH:24][CH:25]4[CH2:30][CH2:29][N:28]([CH2:43][CH2:42][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:27][CH2:26]4)=[O:23])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 19354Methyl vinyl sulfoneHCID 44217941HCID 44217941, compound

Product 1

HCID 44219345HCID 44219345, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-3-piperidin-4-yl-urea (0.05 g, 0.12 mmol), triethylamine (0.02 mL, 0.15 mmol) and methylvinylsulfone (0.016 g, 0.15 mmol) were dissolved in tetrahydrofuran (3 mL) and stirred at ambient temperature for 16 h. Ethyl acetate (10 mL) was added to the reaction mixture and everything subsequently washed with water. The organic phase was dried over sodium sulfate, filtered and the filtrate evaporated. The residue was subjected to column chromatography (basic silica gel, ethyl acetate) to yield the title compound (0.026 g, 41%) as an off-white solid; MS: m/e=508.8 (M+H+).

Workup

  1. washsubsequently washed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-72999c2242974dceb50f057a51abeb62
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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