4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate → 6-(1-(Benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-phenylpicolinic acid

HRID 2178261Notes

Reaction equation

HRID 2178261 reaction equation
[C:1]1([C:7]2[C:8]([C:23]([O:25][CH3:26])=[O:24])=[N:9][C:10]([C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH2:19][NH:20]4)=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][C:37](=[O:48])[O:38]C1C=CC([N+]([O-])=O)=CC=1>CC#N>[S:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][C:37]([N:20]1[C:21]2[C:16](=[CH:15][CH:14]=[C:13]([C:10]3[N:9]=[C:8]([C:23]([OH:25])=[O:24])[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:12][CH:11]=3)[CH:22]=2)[CH2:17][CH2:18][CH2:19]1)=[O:38].[S:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][C:37]([N:20]1[C:21]2[C:16](=[CH:15][CH:14]=[C:13]([C:10]3[N:9]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:12][CH:11]=3)[CH:22]=2)[CH2:17][CH2:18][CH2:19]1)=[O:48]

Participants

5

Reactant 2

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateHCID 59418700Methyl 3-phenyl-6-(1,2,3,4-tetrahydroquinolin-7-yl)picolinate

Product 2

HCID 468410626-(1-(Benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-phenylpicolinic acidHCID 59418756Methyl 6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-phenylpicolinate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-phenyl-6-(1,2,3,4-tetrahydroquinolin-7-yl)picolinate (29H) (17 mg, 0.049 mmol) and 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) (15.5 mg, 0.049 mmol) in anhydrous CH3CN (0.8 mL) was heated to reflux for 6 hours, cooled to rt, concentrated under reduced pressure, and the crude material was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 72:28-55:45, to provide the desired product methyl 6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-phenylpicolinate (29I): 1H NMR (300 MHz, CDCl3) δ 8.23 (1H, d), 8.13 (1H, d), 7.85-7.76 (3H, m), 7.66 (1H, d), 7.48-7.35 (4H, m), 7.34-7.28 (2H, m), 6.89 (1H, d), 3.98 (2H, t), 3.71 (3H, s), 2.85 (2H, t), 2.09 (2H, m).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. concentrationconcentrated under reduced pressure
  4. customthe crude material was purified by column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record
ord-5e2eb5afd2c449288b4b16d856e91991
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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