Acetic Acid → HCID 67316096, compound

HRID 1013766Notes

Reaction equation

HRID 1013766 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]([O:25][C:26]4[C:35]5[C:30](=[CH:31][CH:32]=[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.C(O)(=O)C.[OH-].[Na+]>>[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]([O:25][C:26]4[CH:27]=[CH:28][N:29]=[C:30]5[C:35]=4[NH:34][C:33](=[O:36])[CH:32]=[CH:31]5)=[CH:23][CH:24]=3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 67318157HCID 67318157, compound

Product 1

HCID 67316096HCID 67316096, compound

Conditions

Temperature
85 °C

Procedure

In a 48 mL sealed pressure vessel, was added 4-(4-chlorophenyl)-N-(4-(6-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine (0.280 g, 0.553 mmol), HBr (6.01 mL, 11.1 mmol), and acetic acid (6.34 mL, 11.1 mmol). The mixture was stirred at 85° C. for 1 hour. The reaction was monitored and found complete by LC/MS. The reaction mixture was cooled to RT, carefully basified with 6 N NaOH. Light yellow solids crashed out, which were filtered, rinsed with water and dried in vacuum oven to yield 8-(4-(4-(4-chlorophenyl)phthalazin-1-ylamino)phenoxy)-1,5-naphthyridin-2(1H)-one. The product was used without further purification. MS:[M+H]=492.1; Calc'd 491.9 for C28H18ClN5O2

Workup

  1. customIn a 48 mL sealed pressure vessel
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationwhich were filtered
  4. washrinsed with water
  5. customdried in vacuum oven

Sources & evidence

ORD record
ord-487009f7f1d74259af2f819a44b10725
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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