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Diisopropylethylamine → 6-(4-chlorophenyl)-N-[(2E)-2-cyclopropyl-2-methoxyiminoethyl]-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyrazine-2-carboxamide

HRID 1184409
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HRID 1184409 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[N:10][C:9]=2[O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.Cl.[CH3:34][O:35]/[N:36]=[C:37](\[CH:40]1[CH2:42][CH2:41]1)/[CH2:38][NH2:39]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([NH:39][CH2:38]/[C:37](/[CH:40]3[CH2:42][CH2:41]3)=[N:36]/[O:35][CH3:34])=[O:16])[CH:11]=[N:10][C:9]=2[O:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:20])[F:21])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 66678820(S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylic acidHCID 88536678(2E)-2-cyclopropyl-2-methoxyiminoethanamine;hydrochloride

생성물 1

HCID 573776736-(4-chlorophenyl)-N-[(2E)-2-cyclopropyl-2-methoxyiminoethyl]-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyrazine-2-carboxamide수율 45.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a suspension of (S)-6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)-pyrazine-2-carboxylic acid (0.2 g, 577 μmol, Eq: 1.00) in dimethylformamide (4 ml) were added under argon TBTU (204 mg, 635 μmol, Eq: 1.1), ethyldiisopropylamine (373 mg, 478 μl, 2.88 mmol, Eq: 5) and (E)-2-amino-1-cyclopropylethanone O-methyl oxime hydrochloride (104 mg, 635 μmol, Eq: 1.1) and the mixture was stirred at room temperature for 18 h overnight. The reaction mixture was partitioned between ethyl acetate and 10% aqueous citric acid, the phases were separated and the organic phase was dried over MgSO4; filtered; concentrated and purified by flash chromatography (silica gel, 20 g, 5% to 50% ethyl acetate in heptane) to yield the title compound as white crystals (0.12 g, 45.5%, m.p.: 149-152° C.). MS (EI): 457.1 (M+H).

후처리

  1. additionwere added under argon TBTU (204 mg, 635 μmol, Eq: 1.1)
  2. customThe reaction mixture was partitioned between ethyl acetate and 10% aqueous citric acid
  3. customthe phases were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (silica gel, 20 g, 5% to 50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-6a3fcee012f54e7da9dba0e77b5a5272
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08669254B2

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