Acetic Acid → HCID 59427290, compound

HRID 1042914Notes

Reaction equation

HRID 1042914 reaction equation
[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:24]=[CH:23][C:22]([S: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)=[N:6][CH:7]=1.Br.C(O)(=O)C>>[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:24]=[CH:23][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])[CH:32]=[CH:31]5)=[CH:21][CH:20]=3)=[N:10][N:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 67318189HCID 67318189, compound

Product 1

HCID 59427290HCID 59427290, compound

Conditions

Temperature
85 °C

Procedure

A small reaction vial was charged with 4-(5-chloropyridin-2-yl)-N-(4-(6-methoxy-1,5-naphthyridin-4-ylthio)phenyl)phthalazin-1-amine (50 mg, 0.096 mmol), HBr (1.04 mL, 19.12 mmol), and acetic acid (1.1 mL, 19.12 mmol). The mixture was stirred at 85° C. for 2 hrs. LC/MS showed completion of the reaction. The reaction mixture was poured onto an aqueous sodium bicarbonate solution ice bath and the product was extracted with DCM. The organic layer was dried over sodium sulfate and concentrated to afford 8-(4-(4-(5-chloropyridin-2-yl)phthalazin-1-ylamino)phenylthio)-1,5-naphthyridin-2(1H)-one as yellow solid. MS: [M+H]=509.1; Calc'd for C27H17ClN6OS: 509.

Workup

  1. customA small reaction
  2. customcompletion of the reaction
  3. additionThe reaction mixture was poured onto an aqueous sodium bicarbonate solution ice bath
  4. extractionthe product was extracted with DCM
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-854b29172f11447cabd01e81dbe4dca2
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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