Sodium Hydroxide → 6-{3-[(2-Ethoxy-benzylamino)-methyl]-phenylsulfanyl}-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

HRID 658071Notes

Reaction equation

HRID 658071 reaction equation
[NH2:1][C:2]1[C:11]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:28])=[C:7]([S:19][C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[CH:23]=O)[CH:8]=2)[N:3]=1.[CH2:29]([O:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35])[CH3:30].[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:29]([O:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][NH:35][CH2:23][C:22]1[CH:21]=[C:20]([S:19][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][C:6]=2[F:28])[N:3]=[C:2]([NH2:1])[C:11]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10]3)[CH:27]=[CH:26][CH:25]=1)[CH3:30]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 1234652-EthoxybenzylamineHCID 4311764Sodium borohydrideHCID 866342683-[2-Amino-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-6-ylsulfanyl]-benzaldehyde

Product 1

HCID 578640826-{3-[(2-Ethoxy-benzylamino)-methyl]-phenylsulfanyl}-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[2-Amino-7-fluoro-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-6-ylsulfanyl]-benzaldehyde (40 mg, 0.1 mmol) was dissolved in methanol (1 mL), and then 2-ethoxybenzyl amine (60 μL, 0.38 mmol) was added. The resulting mixture was subjected to μW @ 300W, 130° C. for 12 min. NaBH4 (50 mg, 1.3 mmol) was then added portionwise over 1.5 h. The solvent was removed to yield a residue, to which was added 0.1 N NaOH (5 mL). The resulting mixture was extracted with chloroform (3×). The organic layers were combined and dried with MgSO4 and filtered. The solvent was removed to yield a second residue which was purified on silica gel (2-10% MeOH/dichloromethane) to yield the title compound as a residue.

Workup

  1. customThe solvent was removed
  2. customto yield a residue
  3. extractionThe resulting mixture was extracted with chloroform (3×)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customto yield a second residue which
  8. customwas purified on silica gel (2-10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-dbb16b53c39d4a3a9b15a906ca76c669
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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