Methanol → HCID 59843057, compound

HRID 1878771Notes

Reaction equation

HRID 1878771 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][CH2:18][CH2:19][N:20]1[C:25](=[O:26])[CH:24]=[CH:23][C:22]([C:27]2[CH:28]=[C:29]([CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH:30]=[CH:31][CH:32]=2)=[N:21]1)CO.C1COCC1.CO>CS(C)=O.O.[O-]S([O-])=O.[Na+].[Na+].C(Cl)Cl>[CH:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][CH2:18][CH2:19][N:20]1[C:25](=[O:26])[CH:24]=[CH:23][C:22]([C:27]2[CH:28]=[C:29]([CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH:30]=[CH:31][CH:32]=2)=[N:21]1)=[O:1]

Participants

8

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 59843086HCID 59843086, compound

Product 1

HCID 59843057HCID 59843057, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24437Sodium SulfiteSolvent

Procedure

To a solution of tert-butyl (3-(1-(2-(6-(1,2-dihydroxyethyl)-7-methoxyquinolin-4-yloxy)ethyl)-6-oxo-1,6-dihydropyridazin-3-yl)phenyl)methylcarbamate (30 mg, 53 μmol) in DMSO (0.5 mL)-THF (1 mL)-MeOH (1 mL) was added a solution of NaIO4 (80 mg, 374 μmol) in H2O (0.5 mL). After 5 h, the mixture was diluted with aqueous Na2SO3 (2 mL) and CH2Cl2 (5 mL). The organic layer was separated, the aqueous was extracted with CH2Cl2 (3×5 mL). The combined organic phase was dried over MgSO4, concentrated, and purified on silica (1-6% MeOH in CH2Cl2) to give the product as a film (24 mg). LCMS (ESI pos. ion): calc'd for C29H30N4O6: 530.1; found 531.3 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H), 4.02 (s, 3 H), 4.36 (d, J=5.52 Hz, 2 H), 4.70 (t, J=5.52 Hz, 2 H), 4.81 (t, J=5.27 Hz, 2 H), 5.38 (none, 1H), 5.38 (m, 1 H), 6.73 (d, J=5.02 Hz, 1 H), 7.04 (d, J=9.54 Hz, 1 H), 7.35-7.47 (m, 3 H), 7.60 (d, J=7.53 Hz, 1 H), 7.65-7.73 (m, 2 H), 8.60 (s, 1 H), 8.72 (d, J=5.02 Hz, 1 H), 10.36 (s, 1 H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous was extracted with CH2Cl2 (3×5 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica (1-6% MeOH in CH2Cl2)
  6. customto give the product as a film (24 mg)

Sources & evidence

ORD record
ord-d1027d47708140d4ade8cab762066752
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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