Diethyl Ether → HCID 86647282, compound

HRID 2047398Notes

Reaction equation

HRID 2047398 reaction equation
C(OC(N1CCC(C([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([C:29]4[NH:33][C:32]5[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=5[N:30]=4)[CH:23]=3)[CH2:18][CH2:17]2)=O)CC1)=O)(C)(C)C.CC[O:40][CH2:41][CH3:42]>C(Cl)Cl>[NH:33]1[C:32]2[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=2[N:30]=[C:29]1[C:24]1[CH:23]=[C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:42]3([CH:41]=[O:40])[CH2:20][CH2:21][NH:16][CH2:17][CH2:18]3)[CH2:17][CH2:18]2)[CH:27]=[CH:26][C:25]=1[F:28]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 68670404HCID 68670404, compound

Product 1

HCID 86647282HCID 86647282, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-[3-(1H-Benzoimidazol-2-yl)-4-fluoro-phenyl]-piperazine-1-carbonyl}-piperidine-1-carboxylic acid tert-butyl ester (0.08 g, 0.16 mmol) in DCM (1 mL) 2M HCl in Et2O (3.0 mL) was added and the resulting suspension was stirred at room temperature for 3 days. The reaction was concentrated under reduced pressure, water (8 mL) was added and the solution was concentrated under reduced pressure. The solid was purified by preparative HPLC. HPLC fractions were neutralized with K2CO3 and concentrated. DCM (5 mL) and water (5 mL) were added, organic phase was separated and concentrated to give 44 mg of the title compound (72%).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure, water (8 mL)
  2. additionwas added
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe solid was purified by preparative HPLC
  5. concentrationconcentrated
  6. additionDCM (5 mL) and water (5 mL) were added
  7. customorganic phase was separated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7c87a2dda53b45c9930bc032753a3833
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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