Tetrahydrofuran → HCID 86727068, compound

HRID 2175845Notes

Reaction equation

HRID 2175845 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([F:15])=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@@H:24]1CO)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH3:31]CN(C(C)C)C(C)C.C1COCC1>CCOC(C)=O>[C:10]([C:9]1[C:8]([O:13][CH3:14])=[CH:7][C:6]([F:15])=[C:5]([C@@H:3]2[O:4][CH2:31][C@H:25]3[CH2:24][N:23]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:28][CH2:27][N:26]3[CH2:2]2)[CH:12]=1)#[N:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 24820219(R)-2-Hydroxymethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 86727067HCID 86727067, compound

Product 1

HCID 86727068HCID 86727068, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL flask was added 5-(bromoacetyl)-4-fluoro-2-methoxybenzonitrile (2.00 g, 7.35 mmol), (R)—N-Boc-2-hydroxymethyl-piperazine (3.18 g, 14.7 mmol), DIEA (2.57 mL, 14.7 mmol) and THF (50 mL) and stirred at rt for 1 h; LC analysis of the reaction mixture indicated completion of the reaction. The solution was treated with EtOAc (100 mL), washed with brine, dried (Na2SO4), filtered and concentrated to dryness. The residue was then purified over silica gel with the solvent systems of 5% MeOH in DCM to furnish the desired product. LC/MS: [(M+1)]+=408.

Workup

  1. customcompletion of the reaction
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was then purified over silica gel with the solvent systems of 5% MeOH in DCM

Sources & evidence

ORD record
ord-54f8a34c13d645d99d06df577ba66b5f
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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