Isopropylamine → HCID 90416592, compound

HRID 709980Notes

Reaction equation

HRID 709980 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.[CH:42]([NH2:45])([CH3:44])[CH3:43]>C(Cl)Cl>[CH:42]([NH:45][C:5]1[N:4]=[C:3]([O:2][CH3:1])[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]=1)([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 70297m-Chloroperbenzoic acidHCID 90418683HCID 90418683, compound

Product 1

HCID 90416592HCID 90416592, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example C2 (0.13 g, 0.309 mmol) in DCM (5 mL) was treated portion-wise with mCPBA (0.09 g, 0.37 mmol), stirred at RT overnight, treated with isopropyl amine (0.5 mL) and stirred at RT overnight. The mixture was treated with satd. NaHCO3, extracted with DCM (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to obtain N-isopropyl-4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (63 mg, 47%). MS (ESI) m/z: 432.2 (M+H+).

Workup

  1. stirringstirred at RT overnight
  2. additionThe mixture was treated with satd
  3. extractionNaHCO3, extracted with DCM (2×)
  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-61e43f0a3ea64fa08f5c9d6b8a16c455
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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