Triethylamine → HCID 73213540, compound

HRID 2200894Notes

Reaction equation

HRID 2200894 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:12]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([Cl:30])[CH:23]=2)=[N:13][C:14](S(C)=O)=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]1[C:33]2([CH2:37][CH2:36][NH:35][CH2:34]2)[CH2:32]1.C(N(CC)CC)C>C1COCC1>[CH2:1]([NH:8][C:9]([C:11]1[C:12]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([Cl:30])[CH:23]=2)=[N:13][C:14]([N:35]2[CH2:36][CH2:37][C:33]3([CH2:31][CH2:32]3)[CH2:34]2)=[N:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219231035-Azaspiro(2.4)heptaneHCID 118157494N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-formamide

Product 1

HCID 73213540HCID 73213540, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In absolute anhydrous THF (15 mL) were dissolved N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-formamide (180 mg, 0.41 mmol) and 5-azaspiro[2.4]heptane (59 mg, 0.61 mmol). The solution was cooled in an ice bath, and triethylamine (82 mg, 0.82 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 8 h then was quenched with water. The reaction mixture was extracted with DCM. The organic phase was dried over sodium sulfate and concentrated. The obtained solid was purified by silica gel column chromatography (DCM/methanol=50/1) to give the product as a solid (35 mg, 18% yield).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customthen was quenched with water
  3. extractionThe reaction mixture was extracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained solid was purified by silica gel column chromatography (DCM/methanol=50/1)

Sources & evidence

ORD record
ord-e410efcf56e24c1ead0c9b0894a92abd
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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