Diisopropylethylamine → Tert-butyl 4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate

HRID 447152Notes

Reaction equation

HRID 447152 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:24]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(N(C(C)C)CC)(C)C>CN1CCCC1=O.O>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([NH:13][C:11]([C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([N:34]4[CH2:33][CH2:32][N:31]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:36][CH2:35]4)[S:3][C:4]=3[CH:10]=2)=[O:12])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 672362232-bromo-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide

Product 1

HCID 67235904Tert-butyl 4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Bromo-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide (612.2 mg, 1.56 mmol), N-Boc piperazine (300.8 mg, 1.61 mmol) and diisopropylethylamine (0.3 mL, 1.72 mmol) in N-methyl-2-pyrrolidinone (5.5 mL) was stirred at 120° C. (oil bath) for 4 h, then at room temperature for 18 h. The resulting mixture was diluted with water and the solid separated from the solution. The solid was collected by filtration, dissolved in ethyl acetate, washed with water (2×), then dried, filtered and concentrated. The resulting residue was purified by flash chromatography, eluting with 5% methanol in chloroform to yield tert-butyl 4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazine-1-carboxylate as a brown glassy solid.

Workup

  1. customthe solid separated from the solution
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water (2×)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography
  9. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-88dfa0bcb64247babd58069f475dfdab
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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