4-Chlorobenzylamine → HCID 178522864, compound

HRID 1581557Notes

Reaction equation

HRID 1581557 reaction equation
C[Al](C)C.[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.[OH:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[C:26][CH2:27][OH:28])[N:23]=2)[N:18]=[CH:17][C:16]=1[C:29](OCC)=[O:30]>C(Cl)Cl>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:11][C:29]([C:16]2[CH:17]=[N:18][C:19]3[C:24]([C:15]=2[OH:14])=[N:23][C:22]([C:25]#[C:26][CH2:27][OH:28])=[CH:21][CH:20]=3)=[O:30])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 16682925TrimethylaluminumHCID 178469533HCID 178469533, compound

Product 1

HCID 178522864HCID 178522864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylaluminum (2 M in toluene, 42 μL) is added dropwise to a room temperature solution of 4-chlorobenzylamine (17 μL) in CH2Cl2 (1 mL) under nitrogen. The solution is stirred for 5 minutes before the addition in one portion of ethyl 4-hydroxy-6-(3-hydroxy-1-propynyl)[1,5]naphthyridine-3-carboxylate (Preparation 2, 19 mg). The reaction is stirred at room temperature for 3.5 h. The reaction mixture is partitioned with dil. aq. HCl (2 mL) and extracted with CH2Cl2 (2×2 mL). After drying over MgSO4, the extracts are concentrated under vacuum. The crude residue is flash chromatographed (silica, 10% methanol/CH2Cl2).

Workup

  1. customThe reaction mixture is partitioned with dil. aq. HCl (2 mL)
  2. extractionextracted with CH2Cl2 (2×2 mL)
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe extracts are concentrated under vacuum
  5. customchromatographed (silica, 10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-278cb6c8e4c746abaf39dfc6845e836d
Source dataset
uspto-grants-2004_05
Patent number
US06730682B2

Reaction notes

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