Triethylamine → HCID 86650743, compound

HRID 875205Notes

Reaction equation

HRID 875205 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7](=[N:14][O:15][CH2:16][C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][N:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>ClCCl>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7](=[N:14][O:15][CH2:16][C:17]1[N:22]=[C:21]([NH:23][C:34]([CH:31]2[CH2:33][CH2:32]2)=[O:35])[CH:20]=[CH:19][N:18]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 86650742HCID 86650742, compound

Product 1

HCID 86650743HCID 86650743, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[({[(1-methyl-1H-imidazol-2-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-amine (200 mg, 0.64 mmol), triethylamine (0.18 mL, 1.29 mmol), cyclopropanecarboxylic acid chloride (136 mg, 1.29 mmol) in dichloromethane (10 mL) was stirred 6 h30 at room temperature. After dilution with water (50 mL), the layers were separated and the aqueous layer further extracted with dichloromethane (30 mL). The combined organic layers were dried over MgSO4 and the solvents removed in vacuo. Purification on silica gel afforded N-{2-[({[(1-methyl-1 H-imidazol-2-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-yl}cyclopropanecarboxamide as an oil [19 mg, yield 7%; HPLC/MS: m/z=377 (M+H); log P(HCOOH)=1.50].

Workup

  1. customAfter dilution with water (50 mL), the layers were separated
  2. extractionthe aqueous layer further extracted with dichloromethane (30 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvents removed in vacuo
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-b5c3295625e3439eb264af5c249a8ff7
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

Loading…