1-Methylpyrrolidine → HCID 71736865, compound

HRID 715132Notes

Reaction equation

HRID 715132 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:10]([CH3:21])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([NH:19][CH3:20])[CH:13]=3)=[CH:4][C:3]=1[NH:22][C:23](=[O:28])OC(C)=C.[CH3:29][C:30]([CH3:35])([CH3:34])[CH2:31][CH2:32][NH2:33].CN1CCCC1>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:10]([CH3:21])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([NH:19][CH3:20])[CH:13]=3)=[CH:4][C:3]=1[NH:22][C:23]([NH:33][CH2:32][CH2:31][C:30]([CH3:35])([CH3:34])[CH3:29])=[O:28]

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 197093,3-DimethylbutylamineHCID 89815666HCID 89815666, compound

Product 1

HCID 71736865HCID 71736865, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Heat a solution of prop-1-en-2-yl 2,4-difluoro-5-(2-methyl-7-(methylamino)-1,6-naphthyridin-3-yl)phenylcarbamate (1.449 g, 3.77 mmol), 3,3-dimethylbutylamine (0.572 g, 5.65 mmol), and 1-methylpyrrolidine (0.080 g, 0.942 mmol) in dioxane (30 mL) at 80° C. overnight. Cool to RT, collect the precipitate via filtration and dry. Concentrate the filtrate, treat with DCM, sonicate for 0.5 h, collect the solid via filtration and combine with the solid above to afford the title compound (1.43 g, 89%). 1H NMR (400 MHz, DMSO-d6): δ 8.86 (s, 1H), 8.35 (s, 1H), 8.13 (t, 1H), 8.00 (s, 1H), 7.40 (t, 1H), 8.85-8.82 (m, 1H), 6.52-6.49 (m, 2H), 3.07-3.04 (m, 2H), 2.82 (d, 3H), 2.38 (s, 3H), 1.34-1.30 (m, 2H), 0.87 (s, 9H); MS (ESI) m/z: 428.2 (M+H+).

Workup

  1. customcollect the precipitate
  2. filtrationvia filtration
  3. customdry
  4. concentrationConcentrate the filtrate
  5. additiontreat with DCM
  6. customsonicate for 0.5 h
  7. customcollect the solid
  8. filtrationvia filtration

Sources & evidence

ORD record
ord-3d96fc24e2484c7f84d29562d701fb15
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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