Methylamine → HCID 66605016, compound

HRID 1810226Notes

Reaction equation

HRID 1810226 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:6](C=O)=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.CN.[C:28]([BH3-])#[N:29].[Na+].[C:32]([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][C:18]=2[CH2:32][NH:29][CH3:28])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86662772HCID 86662772, compound

Product 1

HCID 66605016HCID 66605016, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To (2-formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.228 g, 0.65 mmol) and methylamine (2M in THF; 0.5 mL, 0.84 mmol) in CH2Cl2 (3.4 mL) was added sodium cyanoborohydride (0.061 g, 0.97 mmol), followed by acetic acid (1 drop). The reaction was stirred at room temperature overnight, until no starting material was seen by analytical LCMS. The solution was neutralized with saturated aqueous NaHCO3 and extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0ea4b424fc4e4282a7d7f57a441cc487
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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