Triethylamine → HCID 73214618, compound

HRID 2200891Notes

Reaction equation

HRID 2200891 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.C[N:32]1[CH2:35][C:34]2([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:33]1.[CH2:41](N(CC)CC)C>C1COCC1>[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:32]2[CH2:33][C:34]3([CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)[CH2:35]2)[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 580429832-Methyl-2,7-diazaspiro[3.5]nonaneHCID 86342163Avanafil Impurity K

Product 1

HCID 73214618HCID 73214618, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (10 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methyl sulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (152 mg, 0.34 mmol) and 2-methyl-2,7-diazaspiro[3.5]nonane (70 mg, 0.50 mmol). Then triethylamine (68 mg, 0.67 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 4 h. 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 (DCM/methanol=20/1) to give 4-((3-chloro-4-methoxybenzyl)amino)-2-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide as a white solid (16 mg, 9% 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 (DCM/methanol=20/1)

Sources & evidence

ORD record
ord-32484982b6274b5eb08f0e04f4221432
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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