Triethylamine → HCID 86650749, compound

HRID 875214Notes

Reaction equation

HRID 875214 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.[CH2:24](N(CC)CC)[CH3:25].[CH:31]1([C:34]([OH:36])=O)[CH2:33][CH2:32]1.[O:37]1[CH2:42][CH2:41]OCC1>>[CH:41]1([C:42]([N:23]([C:21]2[CH:20]=[CH:19][N:18]=[C:17]([CH2:16][O:15][N:14]=[C:7]([C:6]3[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:22]=2)[C:34]([CH:31]2[CH2:33][CH2:32]2)=[O:36])=[O:37])[CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 312751,4-DioxaneHCID 86650746HCID 86650746, compound

Product 1

HCID 86650749HCID 86650749, compoundYield 8%

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 cyclopropanecarboxylic acid (0.24 mL, 2.60 mmol). After stirring at room temperature for 24 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 N-(cyclopropylcarbonyl)-N-{2-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-yl}cyclopropanecarboxamide [23 mg, yield 8%; HPLC/MS: m/z=445 (M+H); log P(HCOOH)>=1.75].

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-17dda3e0071842269da559ac686886ab
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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