Water → HCID 73214616, compound

HRID 2200889Notes

Reaction equation

HRID 2200889 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[CH2:41][CH2:40][CH2:39][C:34]2([CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:33]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:37]2[CH2:36][CH2:35][C:34]3([CH2:39][CH2:40][CH2:41][N:32]([CH3:31])[CH2:33]3)[CH2:38]2)[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 552653057-Methyl-2,7-diazaspiro(4.5)decaneHCID 86342163Avanafil Impurity K

Product 1

HCID 73214616HCID 73214616, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (10 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide (100 mg, 0.22 mmol) and 7-methyl-2,7-diazaspiro[4.5]decane (42 mg, 0.27 mmol). Triethylamine (68 mg, 0.67 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 4 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=20/1) to give 4-((3-chloro-4-methoxybenzyl)amino)-2-(7-methyl-2,7-diazaspiro[4.5]decan-2-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-formamide as a white solid (20 mg, 17% yield).

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. custompurified by silica gel column chromatography (DCM/methanol=20/1)

Sources & evidence

ORD record
ord-61a3ccbd19504cd4bbc7b3d295403111
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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