4-Chlorobenzylamine → HCID 178432389, compound

HRID 2227167Notes

Reaction equation

HRID 2227167 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=O.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C(OCC)(=O)C>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:14]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([I:12])=[C:8]([CH3:13])[N:7]=3)=[O:16])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469688HCID 178469688, compound

Product 1

HCID 178432389HCID 178432389, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-hydroxy-6-iodo-7-methyl[1,8]naphthyridine-3-carboxylate Prep 4(0.41 g) and 4-chlorobenzylamine (2.50 mL) is heated at 180° C. for 1 h. The reaction is cooled to room temperature. Ethyl acetate (10 mL) and then hexanes (20 mL) are added and the solid is filtered, washed thoroughly with hexanes, and dried. The crude solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (3L), 1.5% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L)) affords the desired product as a white solid (0.30 g, 0.66 mmol, 58%). Physical characteristics are as follows: m.p. 276-277° C.; 1H NMR (300 MHz, DMSO-d6) δ 13.17, 10.10, 8.83, 8.66, 7.40, 7.35, 4.54, 2.77; IR (drift) 3063, 3022, 2957, 2895, 1650, 1596, 1552, 1521, 1493, 1405, 1352, 1323, 1241, 1095, 807 cm−1; MS (ESI) m/z 453.6 (M+H)+, 451.7 (M−H)−; Anal. Calcd for C17H13ClIN3O2: C, 45.01; H, 2.89; N, 9.26; Found: C, 44.92; H, 2.78; N, 9.17.

Workup

  1. filtrationthe solid is filtered
  2. washwashed thoroughly with hexanes
  3. customdried
  4. dissolutionThe crude solid is dissolved in CH2Cl2/MeOH
  5. customPurification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (3L), 1.5% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L))

Sources & evidence

ORD record
ord-3c98c1748dd84fa8a8a47663fee98eb5
Source dataset
uspto-grants-2002_07
Patent number
US06413958B2

Reaction notes

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