Water → HCID 10269737, compound

HRID 1168190Notes

Reaction equation

HRID 1168190 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][OH:22])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.[C:25]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][OH:22])[CH:17]=3)[N:12]([CH3:25])[N:11]=2)=[O:9])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522949HCID 178522949, compound

Product 1

HCID 10269737HCID 10269737, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-cinnolinecarboxamide (Prep. 6, 0.12 g), K2CO3 (0.21 g) and iodomethane (26 μL) in 5 mL anhydrous DMF is heated at 90° C. for 1.5 h. The reaction is cooled to room temperature and poured into 50 mL water. The resulting solid is filtered and dried, then dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1L), 0.5% MeOH/CH2Cl2 (2L), 1% MeOH/CH2Cl2 (1L), 1.5% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (1L), 2.5% MeOH/CH2Cl2 (3L), 3% MeOH/CH2Cl2 (1L), 4% MeOH/CH2Cl2 (1L), 6% MeOH/CH2Cl2 (1L), 8% MeOH/CH2Cl2 (1L)) affords the desired product as a white solid (0.044 g, 36%). Physical characteristics are as follows: m.p. 203-205° C.; 1H NMR (300 MHz, DMSO-d6) δ10.11, 8.23, 7.95, 7.92, 7.40, 5.54, 4.68, 4.56, 4.26; IR (drift) 3380, 1653, 1600, 1551, 1482, 1406, 1351, 1107, 1090, 1015, 813, 801, 727, 709, 659 cm−1; MS (FAB) m/z 358 (MH+), 511, 361, 360, 359, 358, 217, 127, 125, 123, 39; HRMS (FAB) calcd for C18H16ClN3O3+H1 358.0958, found 358.0961.

Workup

  1. filtrationThe resulting solid is filtered
  2. customdried
  3. dissolutiondissolved in CH2Cl2/MeOH
  4. customPurification by chromatography (eluent CH2Cl2 (1L), 0.5% MeOH/CH2Cl2 (2L), 1% MeOH/CH2Cl2 (1L), 1.5% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (1L), 2.5% MeOH/CH2Cl2 (3L), 3% MeOH/CH2Cl2 (1L), 4% MeOH/CH2Cl2 (1L), 6% MeOH/CH2Cl2 (1L), 8% MeOH/CH2Cl2 (1L))

Sources & evidence

ORD record
ord-cf9b8d08635542ed9d925b644b6e7d15
Source dataset
uspto-grants-2003_09
Patent number
US06624160B2

Reaction notes

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