Methanol → HCID 11176268, compound

HRID 639906Notes

Reaction equation

HRID 639906 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11]([O:20][CH2:21][C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:25]=[N:24][CH:23]=3)=[N:10][C:9]=2[C:46]#[N:47])[CH:5]=[CH:6][CH:7]=1.CO>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11]([O:20][CH2:21][C:22]3[NH:26][CH:25]=[N:24][CH:23]=3)=[N:10][C:9]=2[C:46]#[N:47])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 68518147HCID 68518147, compound

Product 1

HCID 11176268HCID 11176268, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(3-fluorophenyl)-6-methoxy-1-[(1-trityl-1H-imidazol-5-yl)methoxy]isoquinoline-3-carbonitrile (255 mg) was dissolved in 4 mL of 5% TFA in CH2Cl2 at 0 C to give a bright yellow solution. The reaction was stirred at 0 C for 2.5 h, then at room temp for 1.5 h. MeOH was added, and the reaction was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The aqueous solution was further extracted with CH2Cl2 (3×). The combined organic solutions were dried over MgSO4 and concentrated. The white solid residue was recrystallized from CH2Cl2-EtOAc to give white solid. The mother liquor was concentrated and purified by flash chromatography (0% to 10% MeOH(10% NH4OH) in EtOAc to give additional white solid.

Workup

  1. customto give a bright yellow solution
  2. waitat room temp for 1.5 h
  3. customthe reaction was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  4. extractionThe aqueous solution was further extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe white solid residue was recrystallized from CH2Cl2-EtOAc
  8. customto give white solid
  9. concentrationThe mother liquor was concentrated
  10. custompurified by flash chromatography (0% to 10% MeOH(10% NH4OH) in EtOAc
  11. customto give additional white solid

Sources & evidence

ORD record
ord-5126f64c4dae48f6b074f1445b239b72
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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