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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Phenol → 2-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-3-methyl-3H-imidazole-4-carboxylic acid phenyl ester

HRID 2222092
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HRID 2222092 반응식
[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
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참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-fac68a616c2e4319a2bfd516b80053c9
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07371749B2

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