Triethylamine → HCID 44537857, compound

HRID 1962400Notes

Reaction equation

HRID 1962400 reaction equation
[CH:1]1([C@H:4]([NH:12][C:13]([C:15]2[C:24]3[C:19](=[C:20]([F:25])[CH:21]=[CH:22][CH:23]=3)[C:18](=[O:26])[N:17]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[C:16]=2[CH2:33]Br)=[O:14])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=2)[CH2:3][CH2:2]1.[C:35]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)([CH3:38])([CH3:37])[CH3:36].C(N(CC)CC)C>C1COCC1>[CH:1]1([C@H:4]([NH:12][C:13]([C:15]2[C:24]3[C:19](=[C:20]([F:25])[CH:21]=[CH:22][CH:23]=3)[C:18](=[O:26])[N:17]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[C:16]=2[CH2:33][N:42]2[CH2:43][CH2:44][N:39]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:40][CH2:41]2)=[O:14])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 35305721-Tert-butylpiperazineHCID 58286948HCID 58286948, compound

Product 1

HCID 44537857HCID 44537857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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, 0.225 mmol) was dissolved in THF (6 mL) mmol) and 1-tert-butyl-piperazine (64.0 mg, 0.450 mmol) and triethylamine (62 μL, 0.44 mmol) were added. The reaction mixture was stirred overnight at room temperature and concentrated in vacuo. The residue was subjected to preperative TLC on silica gel (eluent: 80% ethyl acetate, 10% methanol, 10% triethylamine). The product-containing fraction was dissolved in methanol and the product precipitated on addition of water. After filtration and drying 3-(4-tert-butyl-piperazin-1-ylmethyl)-8-fluoro-1-oxo-2-pyridin-3-yl-1,2-dihydro-isoquinoline-4-carboxylic acid [(S)-cyclopropyl-(3-fluoro-phenyl)-methyl]-amide was obtained.

Workup

  1. additionwere added
  2. concentrationconcentrated in vacuo
  3. dissolutionThe product-containing fraction was dissolved in methanol
  4. customthe product precipitated on addition of water
  5. filtrationAfter filtration
  6. dry with materialdrying 3-(4-tert-butyl-piperazin-1-ylmethyl)-8-fluoro-1-oxo-2-pyridin-3-yl-1,2-dihydro-isoquinoline-4-carboxylic acid [(S)-cyclopropyl-(3-fluoro-phenyl)-methyl]-amide
  7. customwas obtained

Sources & evidence

ORD record
ord-a968c692abe4487ba532696a18f05ed7
Source dataset
uspto-grants-2013_04
Patent number
US08415356B2

Reaction notes

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