Triethylamine → HCID 90947181, compound

HRID 875206Notes

Reaction equation

HRID 875206 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.[CH3:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][C:37](Cl)=[O:38]>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:37](=[O:38])[O:36][CH2:35][CH2:34][CH2:33][CH2:32][CH3:31])[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 69489Pentyl chloroformateHCID 86650742HCID 86650742, compound

Product 1

HCID 90947181HCID 90947181, compoundYield 12%

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), chloroformic acid n-amyl ester (0.19 mL, 1.29 mmol) in dichloromethane (10 mL) was stirred 4 h20 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 pentyl {2-[({[(1-methyl-1H-imidazol-2-yl)(phenyl)methylene]amino}oxy)methyl]pyrimidin-4-yl}carbamate as an oil [34 mg, yield 12%; HPLC/MS: m/z=423 (M+H); log P(HCOOH)=2.28].

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-def5b674a07c4349a26f1f53b8921b04
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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