Hydrochloric Acid → HCID 44599409, compound

HRID 1962401Notes

Reaction equation

HRID 1962401 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[CH:9]1([C@H:12]([NH:20][C:21]([C:23]2[C:32]3[C:27](=[C:28]([F:33])[CH:29]=[CH:30][CH:31]=3)[C:26](=[O:34])[N:25]([C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[C:24]=2[CH2:41]Br)=[O:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[CH2:11][CH2:10]1.Cl>O1CCCC1>[CH:9]1([C@H:12]([NH:20][C:21]([C:23]2[C:32]3[C:27](=[C:28]([F:33])[CH:29]=[CH:30][CH:31]=3)[C:26](=[O:34])[N:25]([C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[C:24]=2[CH2:41][N:3]2[CH2:7][CH2:6][CH2:5][C:4]2=[O:8])=[O:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 58286948HCID 58286948, compound

Product 1

HCID 44599409HCID 44599409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% in mineral oil, 72 mg, 1.8 mmol) was added to 2-pyrrolidinone (380 mg, 4.5 mmol) in tetrahydrofuran (2.0 mL) under an atmosphere of Argon. The reaction mixture was stirred for 30 minutes at room temperature. To this mixture, 3-bromomethyl-8-fluoro-1-oxo-2-pyridin-3-yl-1,2-dihydro-isoquinoline-4-carboxylic acid[(S)-cyclopropyl-(3-fluoro-phenyl)-methyl]-amide (118 mg, 0.23 mmol) in tetrahydrofuran (5 mL) was added dropwise. The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into 25 mL 0.2N HCl (aq). The mixture was extracted with ethyl acetate (25 mL). The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The title compound was isolated by preparative TLC on silica gel (eluent: ethyl acetate).

Workup

  1. stirringThe reaction mixture was stirred for 1 hour at room temperature
  2. extractionThe mixture was extracted with ethyl acetate (25 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5c41a3fc7a14a1bbc8c80f0e2518422
Source dataset
uspto-grants-2013_04
Patent number
US08415356B2

Reaction notes

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