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Phenol → 2-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-3-methyl-3H-imidazole-4-carboxylic acid phenyl ester

HRID 2222092
Notes
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Reaction equation

HRID 2222092 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:16])[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])C=N1.[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[P+](N1CCCC1)(N1CCCC1)[N:26]1CCC[CH2:27]1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C=O.CN(C)C1C=CN=CC=1.ClCCl>[C:17]1([O:15][C:13]([C:11]2[N:26]([CH3:27])[C:7]([CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:16])=[N:8][CH:12]=2)=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 996PhenolHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2733179PyBroPHCID 675495131-{2-[(2-methoxy-ethyl)-methyl-amino]-ethyl}-1H-pyrazole-4-carboxylic acid

Product 1

HCID 585925902-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-3-methyl-3H-imidazole-4-carboxylic acid phenyl ester
Yield 55%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-[(2-methoxy-ethyl)-methyl-amino]-ethyl}-1H-pyrazole-4-carboxylic acid (467 mg, 1.54 mmol) and phenol (145 mg, 1.54 mmol) in dimethylformamide (8 ml) was added under argon at 0° C. a solution of 4-dimethylaminopyridine (94 mg, 0.77 mmol) and brom-tripyrrolidinophosphonium-hexafluorophosphat (790 mg, 0.70 mmol) in dimethylformamide (8 ml) followed by triethylamine (0.65 ml, 4.6 mmol). After 48 h at ambient temperature, the reaction mixture is treated with saturated aqueous ammonium chloride (25 ml) and extracted three times with ethyl acetate (25 ml each). The combined organic layers are dryed with magnesium sulphate and evaporated to dryness. Flash chromatography (silice, eluent dichloromethane containing 4% methanol) afforded the title compound as colorless oil (55% yield). MS: m/e=304(M+H+).

Workup

  1. extractionextracted three times with ethyl acetate (25 ml each)
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-fac68a616c2e4319a2bfd516b80053c9
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07371749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes