Tetrahydrofuran → HCID 118158016, compound

HRID 2200895Notes

Reaction equation

HRID 2200895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][C:17]2N=CC=CN=2)=[O:14])=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.C(N([CH2:36][CH3:37])CC)C.Cl.[O:39]=[C:40]1[CH2:46][CH:45]2[NH:47][CH:42]([CH2:43][CH2:44]2)[CH2:41]1.[CH2:48]1[CH2:52]OC[CH2:49]1>>[CH2:16]([NH:15][C:13]([C:12]1[C:7]([NH:6][CH2:5][C:4]2[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:2]([Cl:1])[CH:3]=2)=[N:8][C:9]([N:47]2[CH:45]3[CH2:44][CH2:43][CH:42]2[CH2:41][C:40](=[O:39])[CH2:46]3)=[N:10][CH:11]=1)=[O:14])[C:17]1[CH:37]=[CH:36][CH:52]=[CH:48][CH:49]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochlorideHCID 86342163Avanafil Impurity K

Product 1

HCID 118158016HCID 118158016, compoundYield 24%

Procedure

In absolute anhydrous THF (30 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (222 mg, 0.5 mmol) and triethylamine (0.25 mL, 1.35 mmol). 3-oxo-8-azabicyclo[3.2.1]octane hydrochloride salt (90 mg, 0.6 mmol) was then added. The reaction was conducted at ambient temperature overnight. The solvent was removed by rotary evaporation, followed by addition of water and extraction with DCM. The organic phase was dried over sodium sulfate and purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to give a white solid (60 mg, 24% yield).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionfollowed by addition of water and extraction with DCM
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. custompurified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-647eb1f03b4141538cb946f25c2f560d
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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