Pyridine → HCID 118080523, compound

HRID 1485783Notes

Reaction equation

HRID 1485783 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][S:37](Cl)(=[O:39])=[O:38]>O1CCOCC1>[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][S:37]([CH3:36])(=[O:39])=[O:38])[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 31297Methanesulfonyl chlorideHCID 118080513HCID 118080513, compound

Product 1

HCID 118080523HCID 118080523, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Pyridine (4.07 μL, 0.050 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 1,4-dioxane (200 μL). Methanesulfonyl chloride (1.96 μL, 0.025 mmol) was added, and the mixture 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 to afford isopropyl (S)-4-acetyl-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-6-(methylsulfonamido)-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.0087 g, 73% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.07-1.16 (m, 6 H), 1.18-1.36 (m, 8H), 2.30 (s, 3 H), 2.99 (s, 3 H), 3.58-3.80 (m, 2 H), 3.84-3.99 (m, 1 H), 4.99-5.08 (m, 1 H), 6.85 (br s, 1 H), 7.49-7.50 (m, 1 H), 7.71 (d, J=4.40 Hz, 2 H), 7.97 (br s, 1 H). MS (ESI, pos. ion) m/z 476 [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

Sources & evidence

ORD record
ord-973da7493e554ddcb0618af7487a2e22
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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