Triethylamine → HCID 86655354, compound

HRID 2190373Notes

Reaction equation

HRID 2190373 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([O:15][C:16]3[CH:17]=[CH:18][C:19]([CH3:36])=[C:20]([NH:22][C:23](=[O:35])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]5([C:33]#[N:34])[CH2:32][CH2:31]5)[CH:25]=4)[CH:21]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)=[O:4].C(N(CC)CC)C.[CH3:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>O1CCCC1.C(OCC)(=O)C>[C:33]([C:30]1([C:26]2[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=2)[C:23]([NH:22][C:20]2[CH:21]=[C:16]([O:15][C:13]3[CH:12]=[CH:11][C:9]4[N:10]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:48]5[CH2:49][CH2:50][N:45]([CH3:44])[CH2:46][CH2:47]5)[S:7][C:8]=4[CH:14]=3)[CH:17]=[CH:18][C:19]=2[CH3:36])=[O:35])[CH2:32][CH2:31]1)#[N:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 86655355HCID 86655355, compound

Product 1

HCID 86655354HCID 86655354, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-[5-({2-[(Chloroacetyl)amino]-1,3-benzothiazol-6-yl}oxy)-2-methylphenyl]-3-(1-cyanocyclopropyl)benzamide synthesized above was dissolved in tetrahydrofuran (5.0 mL), triethylamine (188 μL, 1.36 mmol) and 1-methylpiperazine (152 μL, 1.36 mmol) were added, and the mixture was stirred at 60° C. for 8 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water (100 mL) and saturated brine (100 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and the obtained solution was concentrated under reduced pressure. The obtained residue was triturated with ethyl acetate/hexane to give the title compound (141 mg, 36%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water (100 mL) and saturated brine (100 mL)
  3. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
  7. concentrationthe obtained solution was concentrated under reduced pressure
  8. customThe obtained residue was triturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-b5425f3585a04699a4cdff69f9ffbf86
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…