Acetic Acid → HCID 136381726, compound

HRID 1042893Notes

Reaction equation

HRID 1042893 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([S:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[N:23][N:22]=4)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.Br.C(O)(=O)C.C(=O)(O)[O-].[Na+]>>[C:31]1([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]([NH:20][C:17]3[CH:16]=[CH:15][C:14]([S:13][C:7]4[CH:8]=[CH:9][N:10]=[C:11]5[C:6]=4[N:5]=[CH:4][C:3]([OH:2])=[CH:12]5)=[CH:19][CH:18]=3)=[N:22][N:23]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 25094551HCID 25094551, compound2×

Product 1

HCID 136381726HCID 136381726, compound

Conditions

Temperature
85 °C

Procedure

A reaction vial was charged with N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine (40 mg, 82 μmol), HBr (891 μl, 16408 μmol), and acetic acid (939 μl, 16408 μmol). The vial was sealed, and the reaction mixture was stirred at 85° C. for 2 hrs. Upon cooling, LC/MS analysis showed a mass ion peak corresponding to N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)-4-phenylphthalazin-1-amine (40 mg, 82 μmol). The reaction mixture was poured into an ice-cooled aqueous solution of sodium bicarbonate. Extraction of the product was attempted with DCM. However, the product seemed insoluble in DCM and was present in both the aqueous and organic layers, so all liquid was removed in vacuo. The resulting white solid was taken up in water and filtered. The filtrate was washed several times with water, and the resulting yellow solid was analyzed by LCMS. LCMS analysis showed clean 8-(4-(4-phenylphthalazin-1-ylamino)phenylthio)-1,5-naphthyridin-3-ol. The crude material was carried forward.

Workup

  1. customA reaction
  2. customThe vial was sealed
  3. temperatureUpon cooling
  4. extractionExtraction of the product
  5. customso all liquid was removed in vacuo
  6. filtrationfiltered
  7. washThe filtrate was washed several times with water

Sources & evidence

ORD record
ord-2212838b333c4c81b253481c1f2c28aa
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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