Triethylamine → HCID 66939427, compound

HRID 1257352Notes

Reaction equation

HRID 1257352 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][O:32][CH2:33][C:34](Cl)=[O:35]>O1CCCC1>[CH3:31][O:32][CH2:33][C:34]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 58127606HCID 58127606, compound

Product 1

HCID 66939427HCID 66939427, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an ice-bath, to a solution (4 mL) of the crude compound (0.84 mmol) obtained in Example 36b in tetrahydrofuran were added triethylamine (0.15 mL, 1.1 mmol) and methoxyacetylchloride (110 mg, 1.0 mmol), and the mixture was stirred at room temperature overnight. After confirmation of the termination of the reaction by TLC, the resulting salt was removed. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (hexane-ethyl acetate) to give the title compound (250 mg, 74% in 2 steps) as colorless crystals.

Workup

  1. customAfter confirmation of the termination of the reaction by TLC
  2. customthe resulting salt was removed
  3. customThe solvent was evaporated under reduced pressure
  4. customThe resulting crude title compound was recrystallized (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a1c8090274dc4a06afd0b9fac8635b32
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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