Water → HCID 73214547, compound

HRID 2200888Notes

Reaction equation

HRID 2200888 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]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.[CH2:31]1[C:33]2([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:32]1.C(N(CC)CC)C.O>C1COCC1.C(Cl)Cl>[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]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:14])=[CH:11][N:10]=[C:9]([N:36]2[CH2:37][CH2:38][C:33]3([CH2:31][CH2:32]3)[CH2:34][CH2:35]2)[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 224171736-Azaspiro[2.5]octaneHCID 86342163Avanafil Impurity K

Product 1

HCID 73214547HCID 73214547, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (15 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (134 mg, 0.30 mmol) and 6-azaspiro[2.5]octane (50 mg, 0.45 mmol). Triethylamine (61 mg, 0.60 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 8 h, followed by addition of water and extraction with DCM. The organic phase was dried over sodium sulfate and purified by silica gel column chromatography (DCM/methanol=80/1) to give a white solid (41 mg, 28% yield).

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. custompurified by silica gel column chromatography (DCM/methanol=80/1)

Sources & evidence

ORD record
ord-89cde9189011467ea0919e2b8babd5a3
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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