Methylamine → HCID 68292902, compound

HRID 1504952Notes

Reaction equation

HRID 1504952 reaction equation
[C:1]([C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17]C)=O)=[CH:9][CH:8]=1)([CH3:5])[CH3:4])#[N:2].[CH3:19][NH2:20]>CO>[C:1]([C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]([NH:20][CH3:19])=[O:17])=[CH:11][CH:12]=1)([CH3:4])[CH3:5])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68292605HCID 68292605, compound

Product 1

HCID 68292902HCID 68292902, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of compound 37 (20 mg, 0.08 mmol) in CH3OH (3 mL) was added dropwise a solution of the CH3NH2 in CH3OH (3 mL) at 0° C. with stirring. The reaction mixture was stirred at 0° C. for 6 h. The ice-water was added into the reaction mixture. The aqueous phase was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 38 (25 mg) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.09 (d, 2H, J=8.2 Hz), 6.86 (d, 2H, J=8.2 Hz), 2.90 (t, 2H, J=7.4 Hz), 2.77 (d, 3H, J=4.8 Hz), 2.43 (t, 2H, J=7.4 Hz), 1.68 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 6 h
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cc5f6b14ea1c4024abfbb4a09f3cbb34
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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