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Triethylamine → 3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamide

HRID 1959376
ノート
印刷プレビュー

反応式

HRID 1959376 の反応式
[NH2:1][C:2]1[C:3]([C:19]([OH:21])=O)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.Cl.[CH3:23][O:24][NH:25][CH3:26].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:19]([N:25]([O:24][CH3:23])[CH3:26])=[O:21])=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:6][N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667445273-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

生成物 1

HCID 866620733-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-methoxy-N-methylpyrazine-2-carboxamide収率 76%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (1 g, 3.171 mmol), N-methoxymethanamine hydrochloride (371.2 mg, 3.805 mmol) and triethylamine (705.9 mg, 972.3 μL 6.976 mmol) were dissolved in DMF (10 mL) and treated with TBTU (1.527 g, 4.756 mmol). The mixture was allowed to stir at ambient temperature for 1 hour. The reaction was treated with water, extracted with EtOAc (4×), and the organics separated, dried (MgSO4) and concentrated. The resultant residue was purified on silica gel by flash column chromatography (0-100% EtOAc/Petrol) to afford the title compound as a yellow solid (864 mg, 76% Yield). 1H NMR (400.0 MHz, DMSO) d 1.21 (t, 3H), 3.10 (q, 2H), 3.27-3.30 (m, 4H), 3.34 (s, 3H), 3.38-3.40 (m, 4H), 3.68 (s, 3H), 5.87 (br s, 2H) and 7.99 (s, 1H) ppm; MS (ES+) 359.0

後処理

  1. extractionextracted with EtOAc (4×)
  2. dry with materialthe organics separated, dried (MgSO4)
  3. concentrationconcentrated
  4. customThe resultant residue was purified on silica gel by flash column chromatography (0-100% EtOAc/Petrol)

出典と根拠

ORDレコード
ord-53c32377c07240209d6f963b158c3e83
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410112B2

反応ノート

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