2-(Methylamino)ethanol → 2-((4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)benzyl)(methyl)amino)ethanol

HRID 2193687Notes

Reaction equation

HRID 2193687 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[CH:5][CH:4]=1.[CH3:29][NH:30][CH2:31][CH2:32][OH:33]>COCCOC>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:30]([CH3:29])[CH2:31][CH2:32][OH:33])=[CH:4][CH:5]=3)[S:17][C:16]=12

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 594245202-(4-(Chloromethyl)phenyl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 587901972-((4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)benzyl)(methyl)amino)ethanolYield 62%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 52 (1.2 g, 2.89 mmol) in DME (30 ml) was added 2-(methylamino)ethanol (2.17 g, 10 eq, 28.9 mmol) and the reaction mixture was stirred at RT for 2 hrs. The reaction mixture was concentrated then partitioned between EtOAc/H2O and the EtOAc was collected, dried over Na2SO4, filtered and concentrated. The crude mixture was purified by column chromatography (8:2 EtOAc:MeOH) to afford title compound 85 (813 mg, 45% yield). 1H NMR (DMSO-d6) δ (ppm): 8.57 (d, J=5.48 Hz, 1H), 8.48 (m, 1H), 8.21 (m, 1H), 8.08 (s, 1H), 7.83 (d, J=8.02 Hz, 1H), 7.71 (t, J=8.61 Hz, 2H), 7.43 (d, J=8.22 Hz, 2H), 6.91 (d, J=5.48 Hz, 1H), 4.41 (t, J=5.48 Hz, 1H), 3.53 (m, 4H), 2.42 (t, J=6.46 Hz, 2H), 2.15 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthen partitioned between EtOAc/H2O
  3. customthe EtOAc was collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by column chromatography (8:2 EtOAc:MeOH)

Sources & evidence

ORD record
ord-48ad0ac7c784403eb934b7538d867f19
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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