Hydrochloric Acid → HCID 178424085, compound

HRID 2357645Notes

Reaction equation

HRID 2357645 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:29][N:28]=[N:27][N:26]=2)=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1.C(O)C.C(=O)([O-])[O-].[K+].[K+].O.Cl>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[NH:26][N:27]=[N:28][N:29]=2)=[CH:23][C:24]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[N:7][N:6]=[CH:5]2

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 251930626-Chloro-1-morpholinophthalazineHCID 178424084HCID 178424084, compound

Product 1

HCID 178424085HCID 178424085, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-1-morpholinophthalazine (160 mg, 641 μmol), 5-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-tetrazole (220 mg, 769 μmol), and tetrakis(triphenylphosphine)palladium (74 mg, 64 μmol) were dissolved in ethanol (6408 μl, 641 μmol) and potassium carbonate—2 M in water (1282 μl, 2563 μmol) and heated to 80° C. for 4 h. The reaction mixture was diluted with 20 mL ethyl acetate, partitioned with ammonium chloride (saturated, aqueous), organic layer washed 2 times with 50 mL of ammonium chloride (saturated, aqueous) to give product in the aqueous layer, this was acidified with ca. 3 N HCl to pH 5. The aqueous layer was extracted with chloroform, organic layer separated, dried over sodium sulfate, concentrated in vacuo, and purified via HPLC to give title compound. MS (ES+): 374(M+H)+.

Workup

  1. custompartitioned with ammonium chloride (saturated, aqueous), organic layer
  2. washwashed 2 times with 50 mL of ammonium chloride (saturated, aqueous)
  3. customto give product in the aqueous layer
  4. extractionThe aqueous layer was extracted with chloroform, organic layer
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified via HPLC

Sources & evidence

ORD record
ord-362c9770b55948248009ec3c6a91eede
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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