Triethylamine → HCID 73214619, compound

HRID 2200893Notes

Reaction equation

HRID 2200893 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.[CH3:31][N:32]1[CH2:35][C:34]2([CH2:38][NH:37][CH2:36]2)[CH2:33]1.C(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:37]2[CH2:38][C:34]3([CH2:35][N:32]([CH3:31])[CH2:33]3)[CH2:36]2)[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57856653HCID 57856653, compoundHCID 86342163Avanafil Impurity K

Product 1

HCID 73214619HCID 73214619, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (15 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methyl sulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (120 mg, 0.27 mmol) and 2-methyl-2,6-diazaspiro[3.3]heptane (45 mg, 0.40 mmol). The solution was cooled in an ice bath, and triethylamine (82 mg, 0.81 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 8 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/triethylamine=10/1/0.008) to give 4-((3-chloro-4-methoxybenzyl)amino)-2-(6-methyl-2,6-diazaspiro[3.3]heptan-2-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide as a white solid (35 mg, 26% yield).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe solvent was removed by rotary evaporation
  3. additionfollowed by addition of water and extraction with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. custompurified by silica gel column chromatography (DCM/methanol/triethylamine=10/1/0.008)

Sources & evidence

ORD record
ord-8ce7ff12c66d4ec49957ab022bb5dbad
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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