Water → HCID 9955567, compound

HRID 1168185Notes

Reaction equation

HRID 1168185 reaction equation
IC.[Cl:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([I:23])=[CH:17][CH:16]=3)=[O:11])=[CH:6][CH:5]=1.[C:26]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([I:23])[CH:19]=3)[N:14]([CH3:26])[N:13]=2)=[O:11])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522950HCID 178522950, compound

Product 1

HCID 9955567HCID 9955567, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Iodomethane (0.028 mL) is added to a suspension of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-cinnolinecarboxamide; (Prep. 4, 0.16 g) and K2CO3 (0.20 g,) in 6 mL anhydrous DMF. The reaction is heated at 90° C. for 1 h. The reaction is cooled to room temperature and poured into 75 mL H2O. The resulting yellow solid is filtered and dried. The solid is dissolved in CH2Cl2 and adsorbed onto silica. Purification by chromatography (CH2Cl2 (2L), 0.5% MeOH/CH2Cl2 (2L), 0.75% MeOH/CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 1.5% MeOH/CH2Cl2 (1L), 3.5% MeOH/CH2Cl2 (1L), 10% MeOH/CH2Cl2 (1L)) affords the product as an off-white solid (0.062 g, 39%). Physical characteristics are as follows: m.p. 194-195° C.; 1H NMR (300 MHz, DMSO-d6) δ9.86, 8.52, 8.24, 7.76, 7.40, 7.38, 4.55, 4.22; IR (drift) 1671, 1601, 1589, 1549, 1544, 1490, 1463, 1412, 1320, 1278, 1180, 819, 808, 723, 666 cm−1; MS (ESI) m/z 453.7 (M+H)+, 452.8 (M−H)−; Anal. Calcd for C17H13ClIN3O2: C, 45.01; H, 2.89; N, 9.26; Found: C, 44.63; H, 2.98; N, 8.91.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationThe resulting yellow solid is filtered
  3. customdried
  4. dissolutionThe solid is dissolved in CH2Cl2
  5. customPurification by chromatography (CH2Cl2 (2L), 0.5% MeOH/CH2Cl2 (2L), 0.75% MeOH/CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 1.5% MeOH/CH2Cl2 (1L), 3.5% MeOH/CH2Cl2 (1L), 10% MeOH/CH2Cl2 (1L))

Sources & evidence

ORD record
ord-7dfe854478cf4453886d2c5f7f3a9b2c
Source dataset
uspto-grants-2003_09
Patent number
US06624160B2

Reaction notes

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