Methylamine → HCID 45111495, compound

HRID 386911Notes

Reaction equation

HRID 386911 reaction equation
[CH3:1][C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:25])[C:13]([CH3:24])([S:15]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH3:14])[O:8][N:7]=1)([CH3:5])[CH:3]=O.CN.[C:28]([BH3-])#[N:29]>C1COCC1>[CH3:1][C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:25])[C:13]([CH3:14])([S:15]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH3:24])[O:8][N:7]=1)([CH3:5])[CH2:3][NH:29][CH3:28]

Participants

5

Reactant 3

HCID 6329Methylamine2×HCID 498716Cyano-borohydride2×HCID 59253148HCID 59253148, compound

Product 1

HCID 45111495HCID 45111495, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (50 mg, 0.13 mmol) (see Amide Method G) in THF (0.5 mL) is added methylamine (2M solution in THF, 0.25 mL, 0.5 mmol) and 2.44 mmol/g of MP-cyanoborohydride (137 mg, 0.34 mmol). The reaction mixture is placed on a shaker for 2 h. After this time, more methylamine (2 M solution in THF, 0.13 mL, 0.26 mmol) and 2.44 mmol/g of MP-cyanoborohydride (137 mg, 0.34 mmol) are added to the reaction mixture and the stirring is continued for 18 hs. After this time, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure. Purification by preparative HPLC provides the title compound. Yield: 21%; m/z 388 [M+H].

Workup

  1. filtrationAfter this time, the reaction mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-b6bb63a8bda443179db0d8d7b1cc76a6
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

Loading…