Methylamine → HCID 89462644, compound

HRID 1473248Notes

Reaction equation

HRID 1473248 reaction equation
[Si]([O:8][CH2:9][C:10]1[O:15][C:14](=O)[C:13]2[S:17][C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[C:12]=2[C:11]=1[C:24]1[C:25]([CH3:34])=[C:26]2[C:31](=[CH:32][CH:33]=1)[O:30][CH2:29][CH2:28][CH2:27]2)(C(C)(C)C)(C)C.[CH3:35][NH2:36]>CCO>[OH:8][CH2:9][C:10]1[N:36]([CH3:35])[C:14](=[O:15])[C:13]2[S:17][C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[C:12]=2[C:11]=1[C:24]1[C:25]([CH3:34])=[C:26]2[C:31](=[CH:32][CH:33]=1)[O:30][CH2:29][CH2:28][CH2:27]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89463676HCID 89463676, compound

Product 1

HCID 89462644HCID 89462644, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

3-(((tert-butyldimethylsilyl)oxy)methyl)-4-(5-methylchroman-6-yl)-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-one (100 mg, 0.2 mmol) was dissolved in 4N MeNH2 (g)/EtOH (20 mL) and stirred at 65° C. for 3 hrs. After cooling to room temperature, the mixture was concentrated, and 4N HCl/ethyl acetate (20 ml) was added. The mixture was stirred at room temperature for 15 min and concentrated in vacuo. The residue was partitioned between ethyl acetate and sat. aq. NaHCO3 and the organic layer washed with water, dried over Na2SO4 and evaporated to afford the crude title product (60 mg, 75% yield) which was used for the next step directly. LCMS (m/z) ES+=396 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. addition4N HCl/ethyl acetate (20 ml) was added
  4. stirringThe mixture was stirred at room temperature for 15 min
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between ethyl acetate and sat. aq. NaHCO3
  7. washthe organic layer washed with water
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-506a432bf75b4d3ea7c29ac0ca22ad32
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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