Triethylamine → HCID 56840017, compound

HRID 2359344Notes

Reaction equation

HRID 2359344 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]([NH2:29])=[O:28])[CH:25]=3)[CH:20]=[N:19][CH:18]=2)[CH2:13][CH2:12]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO.O>[OH:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]([NH2:29])=[O:28])[CH:25]=3)[CH:20]=[N:19][CH:18]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 56840016HCID 56840016, compound

Product 1

HCID 56840017HCID 56840017, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

4-{4-[2-(Tetrahydro-2H-pyran-2-yloxy)ethoxy]piperidin-1-yl}isoquinoline-6-carboxamide (330 mg, 0.83 mmol) produced in Example 19 was dissolved in methanol-water (90:10, V/V, 15 mL), to which p-toluenesulfonic acid monohydrate (213 mg, 1.24 mmol) was then added, followed by stirring at room temperature for 24 hours. After addition of triethylamine (300 μL), the solvent was distilled off under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (ethyl acetate:methanol, 100:0-80:20, V/V) to give the desired title compound (160 mg, yield 61%).

Workup

  1. additionwas then added
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by basic silica gel column chromatography (ethyl acetate:methanol, 100:0-80:20, V/V)

Sources & evidence

ORD record
ord-9539e048e96c4ad98baa65a2cb24face
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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