Diisopropylethylamine → HCID 73214617, compound

HRID 2200890Notes

Reaction equation

HRID 2200890 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.CCN(C(C)C)C(C)C.[CH3:40][N:41]1[CH2:45][CH2:44][C:43]2([CH2:49][CH2:48][NH:47][CH2:46]2)[CH2:42]1>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:47]2[CH2:48][CH2:49][C:43]3([CH2:44][CH2:45][N:41]([CH3:40])[CH2:42]3)[CH2:46]2)[N:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 47135002-Methyl-2,7-diazaspiro(4.4)nonaneHCID 86342163Avanafil Impurity K

Product 1

HCID 73214617HCID 73214617, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In DCM (30 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (429 mg, 0.96 mmol) and DIEA (0.22 mL, 1.12 mmol). 2-Methyl-2,7-diazaspiro[4.4]nonane (154 mg, 1.1 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 ethyl acetate. The organic phase was dried over sodium sulfate and purified by silica gel column chromatography (DCM/methanol=20/1 to 10/1) to give a white solid (20 mg, 4% yield).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionfollowed by addition of water and extraction with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. custompurified by silica gel column chromatography (DCM/methanol=20/1 to 10/1)

Sources & evidence

ORD record
ord-c60a9ccf37364aeaa81803ca0a5500f8
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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