Sodium Sulfate → HCID 11304999, compound

HRID 403047Notes

Reaction equation

HRID 403047 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:34])=[C:11]([NH:13][C:14]([C:16]3[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]4[CH:31]=[CH:30][C:25]([C:26](OC)=[O:27])=[CH:24][N:23]=4)=[CH:18][CH:17]=3)=[O:15])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:34])=[C:11]([NH:13][C:14](=[O:15])[C:16]3[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]4[CH:31]=[CH:30][C:25]([CH2:26][OH:27])=[CH:24][N:23]=4)=[CH:32][CH:33]=3)[CH:12]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 11487979HCID 11487979, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11304999HCID 11304999, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 6-({4-[({5-[(cyclopropylamino)carbonyl]-2-methylphenyl}amino)carbonyl]phenoxy}methyl)nicotinate (200 mg, 0.436) in THF (10 mL) was added LiAlH4 (33 mg, 0.871 mmol). Extra THF (7 mL) was added and the mixture was stirred for 16 h at room temperature. Glauber's salt (Na2SO4.10H2O) (1.0 g, 3.11 mmol) was added and the reaction was stirred for a further 16 h. The mixture was filtered and the solid washed with methanol (40 mL). The filtrates were evaporated and the resulting crude material was purified by SCX cartridge to give the title compound as a white solid (150 mg, 80%); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.67 (m, 2H), 2.25 (s, 3H), 2.85 (m, 1H), 4.56 (d, 2H), 5.28 (s, 2H), 5.59 (t, 1H), 7.15 (d, 2H), 7.34 (d, 1H), 7.51 (d, 1H), 7.64 (m, 1H), 7.79 (m, 2H), 7.97 (m, 2H), 8.37 (d, 1H), 8.55 (s, 1H), 9.83 (s, 1H); Mass Spectrum: M+H+ 432.

Workup

  1. stirringthe reaction was stirred for a further 16 h
  2. filtrationThe mixture was filtered
  3. washthe solid washed with methanol (40 mL)
  4. customThe filtrates were evaporated
  5. customthe resulting crude material was purified by SCX cartridge

Sources & evidence

ORD record
ord-74b8f7867ae84ed4af6311f04ac17757
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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