Triethylamine → HCID 131732582, compound

HRID 875213Notes

Reaction equation

HRID 875213 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][N:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][N:4]=[CH:3]1.C(N(CC)CC)C.[CH2:31]([O:36][C:37](Cl)=[O:38])[CH2:32][CH2:33][CH2:34][CH3:35]>O1CCOCC1>[CH2:31]([O:36][C:37](=[O:38])[NH:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([CH2:16][O:15][N:14]=[C:7]([C:6]2[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:22]=1)[CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69489Pentyl chloroformateHCID 86650746HCID 86650746, compound

Product 1

HCID 131732582HCID 131732582, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-amine (200 mg, 0.65 mmol) in 1,4-dioxane (10 mL) were sequentially added triethylamine (0.18 mL, 1.30 mmol) and chloroformic acid pentyl ester (0.38 mL, 2.60 mmol). After stirring at room temperature for 19 h, the mixture was concentrated in vacuo, diluted in ethyl acetate (50 mL), washed with water (20 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification on silica gel afforded pentyl{2-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-yl}carbamate [26 mg, yield 9%; HPLC/MS: m/z=423 (M+H); log P(HCOOH)=2.66].

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted in ethyl acetate (50 mL)
  3. washwashed with water (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness in vacuo
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-59abf8edeaa246f19bfeb0120035d7a4
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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