Acetic Acid → HCID 59427323, compound

HRID 1042915Notes

Reaction equation

HRID 1042915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[C:35]5[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36]C)[N:34]=5)[N:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.Br.CC(O)=O.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([S:25][C:26]4[CH:27]=[CH:28][N:29]=[C:30]5[C:35]=4[NH:34][C:33](=[O:36])[C:32]([O:38][CH3:39])=[CH:31]5)=[CH:23][CH:24]=3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 67318545HCID 67318545, compound

Product 1

HCID 59427323HCID 59427323, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

4-(4-Chlorophenyl)-N-(4-(6,7-dimethoxy-1,5-naphthyridin-4-ylthio)phenyl)phthalazin-1-amine (40 mg, 72 μmol) was added to a pyrex reaction tube along with 2 mL of 1:1 HBr:AcOH. The tube was sealed and the mixture was heated at 85° C. for 1.5 h. Upon cooling the mixture was diluted with water and brought to basic pH by dropwise addition of 6N NaOH. The solids were filtered, washed with water, and dried. The crude material was purified by silica gel chromatography, 10-50% 90/10/1 DCM/MeOH/NH4OH in DCM to provide 8-(4-(4-(4-chlorophenyl)phthalazin-1-ylamino)phenylthio)-3-methoxy-1,5-naphthyridin-2(1H)-one as a light yellow solid. MS: [M+H]=539.

Workup

  1. customThe tube was sealed
  2. temperatureUpon cooling the mixture
  3. filtrationThe solids were filtered
  4. washwashed with water
  5. customdried
  6. customThe crude material was purified by silica gel chromatography, 10-50% 90/10/1 DCM/MeOH/NH4OH in DCM

Sources & evidence

ORD record
ord-eb2585e4d2434e7da721cf4044e812d6
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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