Triethylamine → methyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-3-bromopicolinate

HRID 1778911Notes

Reaction equation

HRID 1778911 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH:21]([CH3:23])[NH:20][CH2:19][CH2:18]2)=[O:12].[Br:24][C:25]1[C:26]([C:32]([O:34][CH3:35])=[O:33])=[N:27][C:28](F)=[CH:29][CH:30]=1.C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH:21]([CH3:23])[N:20]([C:28]1[N:27]=[C:26]([C:32]([O:34][CH3:35])=[O:33])[C:25]([Br:24])=[CH:30][CH:29]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 46311213Methyl 3-bromo-6-fluoropicolinateHCID 89498364N-(benzo[d]thiazol-2-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline-8-carboxamide

Product 1

HCID 89498038methyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-3-bromopicolinate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A solution of EXAMPLE 163C (1 g), methyl 3-bromo-6-fluoropicolinate (0.715 g) and triethylamine (0.775 mL) in 12 mL DMSO was heated at 70° C. overnight followed by heating at 105° C. for 4 hours. The reaction mixture was diluted with ethyl acetate, washed three times with water and brine, dried over Na2SO4, filtered, and concentrated. The product was purified by flash chromotography (silica gel, 5-25% ethyl acetate/hexanes).

Workup

  1. washwashed three times with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromotography (silica gel, 5-25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-84c04b0920314131ac3bb59aee2a16b0
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

Loading…