Sodium Hydroxide → 3-(Tetrahydro-pyran-4-ylmethyl)-6-{3-[(2,4,6-trimethyl-benzylamino)-methyl]-phenylsulfanyl}-quinolin-2-ylamine

HRID 658064Notes

Reaction equation

HRID 658064 reaction equation
O1CCCO[CH:2]1[C:7]1[CH:8]=[C:9]([S:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([NH2:24])[C:18]([CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:17]3)[CH:10]=[CH:11][CH:12]=1.[CH3:32][C:33]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[C:34]=1[CH2:35][NH2:36].[OH-].[Na+]>C(O)(=O)C>[O:29]1[CH2:30][CH2:31][CH:26]([CH2:25][C:18]2[C:19]([NH2:24])=[N:20][C:21]3[C:16]([CH:17]=2)=[CH:15][C:14]([S:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH2:2][NH:36][CH2:35][C:34]4[C:37]([CH3:42])=[CH:38][C:39]([CH3:41])=[CH:40][C:33]=4[CH3:32])[CH:8]=2)=[CH:23][CH:22]=3)[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4584332,4,6-TrimethylbenzylamineHCID 689785646-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine

Product 1

HCID 441594033-(Tetrahydro-pyran-4-ylmethyl)-6-{3-[(2,4,6-trimethyl-benzylamino)-methyl]-phenylsulfanyl}-quinolin-2-ylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-3-(tetrahydro-pyran-4-ylmethyl)-quinolin-2-ylamine (40 mg, 0.1 mmol) was dissolved in acetic acid (1 mL) and then 2,4,6-trimethylbenzyl amine (0.1 g, 0.67 mmol) was added. The resulting mixture was subjected to μwave @ 300W, 100° C. for 12 min. The resulting mixture was evaporated under reduced pressure (high vacuum) overnight. Methanol (2 mL) was added, followed by addition of NaBH4 (0.2 g, 5.2 mmol, 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 then filtered. The solvent was removed to yield the title compound as a residue, which was purified by reverse phase chromatography (10-90% CH3CN/H2O/0.1% TFA). The product containing fractions were treated with 1N HCl (1 mL) to yield the title compound, 3-(tetrahydro-pyran-4-ylmethyl)-6-{3-[(2,4,6-trimethyl-benzylamino)-methyl]-phenylsulfanyl}-quinolin-2-ylamine, as a residue.

Workup

  1. customfor 12 min
  2. customThe resulting mixture was evaporated under reduced pressure (high vacuum) overnight
  3. additionMethanol (2 mL) was added
  4. additionfollowed by addition of NaBH4 (0.2 g, 5.2 mmol
  5. customThe solvent was removed
  6. customto yield a residue
  7. extractionThe resulting mixture was extracted with chloroform (3×)
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customThe solvent was removed

Sources & evidence

ORD record
ord-fd808029904f42c5941317b1f2d837db
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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