Triethylamine → HCID 67549168, compound

HRID 43849Notes

Reaction equation

HRID 43849 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:9]=[C:10]([C:15]([NH:17][C@@H:18]2[CH2:23][CH2:22][N:21](C(=O)C(F)(F)F)[CH2:20][C@@H:19]2[NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:16])[NH:11][C:12]=1[CH2:13][CH3:14].C(N(CC)CC)C.Br[C:46]1[S:47][C:48]2[C:54]([C:55]([O:57][CH2:58][CH3:59])=[O:56])=[CH:53][CH:52]=[CH:51][C:49]=2[N:50]=1>CO>[C:33]([O:32][C:31]([NH:30][C@@H:19]1[C@H:18]([NH:17][C:15]([C:10]2[NH:11][C:12]([CH2:13][CH3:14])=[C:8]([Cl:7])[N:9]=2)=[O:16])[CH2:23][CH2:22][N:21]([C:46]2[S:47][C:48]3[C:54]([C:55]([O:57][CH2:58][CH3:59])=[O:56])=[CH:53][CH:52]=[CH:51][C:49]=3[N:50]=2)[CH2:20]1)=[O:37])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67073467Ethyl 2-bromobenzo[d]thiazole-7-carboxylateHCID 86648784tert-Butyl [(3S,4R)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1-(trifluoroacetyl)piperidin-3-yl]carbamate

Product 1

HCID 67549168HCID 67549168, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (40 mg, 0.289 mmol) was added to a solution of tert-butyl [(3S,4R)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-1-(trifluoroacetyl)piperidin-3-yl]carbamate obtained in Example (202c) (123 mg, 0.263 mmol) in methanol (5 mL), and the mixture was heated under reflux at room temperature for three hours. The reaction solution was concentrated under reduced pressure, and then the filtrate was dissolved in dimethylformamide (2 mL). Triethylamine (145 μL, 1.04 mmol) and ethyl 2-bromo-1,3-benzothiazole-7-carboxylate obtained in Example (1f) (82.1 mg, 0.287 mmol) were added at room temperature, and the mixture was stirred at 70° C. for three hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was suspended in ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=1:3) to obtain 121 mg of the title compound (80%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe filtrate was dissolved in dimethylformamide (2 mL)
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationthe filtrate was concentrated
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-69c13ac3f09244e092756e96045babdd
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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