2-Methoxyethylamine → HCID 90417572, compound

HRID 709985Notes

Reaction equation

HRID 709985 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5](SC)[N:4]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:42][O:43][CH2:44][CH2:45][NH2:46]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5]([NH:46][CH2:45][CH2:44][O:43][CH3:42])[N:4]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 70297m-Chloroperbenzoic acidHCID 90418683HCID 90418683, compound

Product 1

HCID 90417572HCID 90417572, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example C2 (0.15 g, 0.36 mmol) in DCM (5 mL) was treated portion-wise with mCPBA (0.11 g, 0.43 mmol), stirred at RT overnight, treated with 2-methoxyethanamine (0.5 mL) and stirred at RT for 4 h. The mixture was treated with satd. NaHCO3, extracted with DCM (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to obtain 4-methoxy-N-(2-methoxyethyl)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (100 mg, 63%). MS (ESI) m/z: 448.2 (M+H+).

Workup

  1. stirringstirred at RT for 4 h
  2. additionThe mixture was treated with satd
  3. extractionNaHCO3, extracted with DCM (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-506e2818517a4e7daba9d79875b6c1f7
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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