Methanol → 6-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

HRID 658063Notes

Reaction equation

HRID 658063 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[CH:15]=[CH:16][C:17]([N+:31]([O-])=O)=[C:18]([CH:20]=[C:21]([CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:22]#[N:23])[CH:19]=2)[CH:10]=[CH:11][CH:12]=1.[NH4+].[Cl-].CO>[Zn].C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[CH:19]=[C:18]3[C:17](=[CH:16][CH:15]=2)[N:31]=[C:22]([NH2:23])[C:21]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:20]3)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 687376013-[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

Product 1

HCID 689785646-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In four μwave tubes, 3-[5-(3-[1,3]dioxan-2-yl-phenylsulfanyl)-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile (0.175 g, 0.375 mmol, each tube), Zn (2.5 g, 0.038 mol, each tube), NH4Cl (0.8 g, 0.015 mol, each tube), CH3OH (3 mL, in each tube) and THF (3 mL, in each tube) was reacted via μwave at 300W, 150° C. for 11 min. The resulting mixtures were combined and then filtered through Celite®. The solvent was removed to yield a residue which was purified by reverse phase column chromatography (10-90% CH3CN/H2O/0.1% TFA) to yield a solid.

Workup

  1. filtrationfiltered through Celite®
  2. customThe solvent was removed
  3. customto yield a residue which
  4. customwas purified by reverse phase column chromatography (10-90% CH3CN/H2O/0.1% TFA)
  5. customto yield a solid

Sources & evidence

ORD record
ord-74771c349847435e868ccc3c86b47a30
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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