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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
ノート
印刷プレビュー

反応式

HRID 1184409 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6a3fcee012f54e7da9dba0e77b5a5272
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08669254B2

反応ノート

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