4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate → Methyl 6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-(2-phenoxyethoxy)picolinate

HRID 1641085Notes

Reaction equation

HRID 1641085 reaction equation
[O:1]([CH2:8][CH2:9][O:10][C:11]1[C:12]([C:27]([O:29][CH3:30])=[O:28])=[N:13][C:14]([C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][CH2:23][NH:24]3)=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[NH:40][C:41](=O)[O:42]C1C=CC([N+]([O-])=O)=CC=1>C(#N)C>[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=[C:32]1[NH:40][C:41]([N:24]1[C:25]2[C:20](=[CH:19][CH:18]=[C:17]([C:14]3[N:13]=[C:12]([C:27]([O:29][CH3:30])=[O:28])[C:11]([O:10][CH2:9][CH2:8][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:16][CH:15]=3)[CH:26]=2)[CH2:21][CH2:22][CH2:23]1)=[O:42]

Participants

4

Reactant 2

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateHCID 59418754Methyl 3-(2-phenoxyethoxy)-6-(1,2,3,4-tetrahydroquinolin-7-yl)picolinate

Product 1

HCID 59418694Methyl 6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-(2-phenoxyethoxy)picolinateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-(2-phenoxyethoxy)-6-(1,2,3,4-tetrahydroquinolin-7-yl)picolinate (27C) (81 mg, 0.2 mmol) and 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) (127 mg, 0.4 mmol) were heated to reflux in acetonitrile (5 mL) for 24 hours. After cooling, the mixture was concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a gradient of PE (100%) to PE/EtOAc (4:6), to provide 114 mg (97%) of the desired product methyl 641-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-(2-phenoxyethoxy)picolinate (27D). 1H NMR (300 MHz, CDCl3) δ8.12 (1H, s), 7.85 (1H, d), 7.73 (1H, m), 7.44 (3H, m), 7.29 (4H, m), 7.09 (1H, m), 6.94 (3H, m), 4.44 (2H, m), 4.37 (2H, m), 3.88 (2H, m), 3.78 (3H, m), 2.74 (2H, m), 2.00 (2H, m).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel eluting with a gradient of PE (100%) to PE/EtOAc (4:6)

Sources & evidence

ORD record
ord-4875480299cb4e689c64ffc1fea05521
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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