4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate → Tert-butyl 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate

HRID 2178240Notes

Reaction equation

HRID 2178240 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:17]=[C:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][C:35](=O)[O:36]C1C=CC([N+]([O-])=O)=CC=1>C(#N)C>[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][C:35]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3[N:17]=[C:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=3)[CH:7]=2)[N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:36]

Participants

4

Reactant 2

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateHCID 59418755Tert-butyl 6-(1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate

Product 1

HCID 59418667Tert-butyl 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinateYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl 6-(1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate (25G) (36 mg, 0.11 mmol) and 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) (42 mg, 0.13 mmol) in anhydrous acetonitrile (1.0 mL) was heated to reflux for 3 hours, cooled to rt, concentrated under reduced pressure, and the crude material was purified by flash column chromatography on silica gel eluting with a gradient of PE:EtOAc 100:0-70:30, to provide 47 mg (85%) of the desired product tert-butyl 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate (25H): 1H NMR (300 MHz, CDCl3) δ 8.14 (1H, s), 7.88-7.77 (2H, m), 7.74 (2H, d), 7.54 (1H, d), 7.34 (1H, t), 7.22 (1H, t), 6.71 (1H, d), 3.97 (2H, t), 3.49 (2H, t), 3.02 (3H, s), 1.56 (9H, s).

Workup

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

Sources & evidence

ORD record
ord-4ec840ae22f14c938aacd72503c4a0f0
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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