Pyridine → HCID 118080517, compound

HRID 1485785Notes

Reaction equation

HRID 1485785 reaction equation
N1C=CC=CC=1.[C:7]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:28][CH2:27]4)[CH:25]=3)=[C:17]([NH2:20])[CH:18]=2)[N:13]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:12][C@@H:11]1[CH3:35])(=[O:9])[CH3:8].[CH3:36][NH:37][C:38](Cl)=[O:39]>ClCCl>[C:7]([N:10]1[C:19]2[C:14](=[CH:15][C:16]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:28][CH2:27]4)[CH:25]=3)=[C:17]([NH:20][C:38]([NH:37][CH3:36])=[O:39])[CH:18]=2)[N:13]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:12][C@@H:11]1[CH3:35])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 80931Methylcarbamoyl chlorideHCID 118080513HCID 118080513, compound

Product 1

HCID 118080517HCID 118080517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (5.09 μL, 0.063 mmol) was added to a solution of isopropyl (S)-4-acetyl-6-amino-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.010 g, 0.025 mmol) in dichloromethane (200 μL). Methylcarbamic chloride (0.003 g, 0.030 mmol) was added, and the reaction stirred at rt for 18 h. The reaction mixture was concentrated and ethyl acetate was added. The solution was washed with 1 N aqueous HCl, and the organic phase was separated and concentrated. The residue was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated in a Genevac to afford isopropyl (S)-4-acetyl-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-6-(3-methylureido)-3,4-dihydroquinoxaline-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 455 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added
  3. washThe solution was washed with 1 N aqueous HCl
  4. customthe organic phase was separated
  5. concentrationconcentrated
  6. customThe residue was purified by mass
  7. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-432ebbf0a9c2400199b903d4dbb6e2e1
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

Loading…