Pyridine → HCID 118080534, compound

HRID 1485784Notes

Reaction equation

HRID 1485784 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].[C:36](OC(=O)C)(=[O:38])[CH3:37]>ClCCl>[C:36]([NH:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[C:21]1[CH:22]=[N:23][N:24]([CH:26]3[CH2:28][CH2:27]3)[CH:25]=1)[N:13]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:12][C@H:11]([CH3:35])[N:10]2[C:7](=[O:9])[CH3:8])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 118080513HCID 118080513, compound

Product 1

HCID 118080534HCID 118080534, 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). Acetic anhydride (3.56 μL, 0.038 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)-6-acetamido-4-acetyl-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 440 [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-91d896a2a713467985bd811c215be701
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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