1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58084376、化合物

HRID 2174658ノート

反応式

HRID 2174658 の反応式
[NH2:1][C:2]1[C:3]([C:20](O)=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.Cl.[CH3:24][O:25][NH:26][CH3:27].O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C(N=C=NCCCN(C)C)C>C1COCC1>[NH2:1][C:2]1[C:3]([C:20]([N:26]([O:25][CH3:24])[CH3:27])=[O:21])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 58084374HCID 58084374、化合物

生成物 1

HCID 58084376HCID 58084376、化合物収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-Amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carboxylic acid (10 g, 31.12 mmol) was dissolved in THF (80 mL) and cooled to 0° C. N-methoxymethanamine hydrochloride (3.642 g, 37.34 mmol), 1-hydroxybenzotriazole hydrate (5.242 g, 34.23 mmol), DIPEA (8.044 g, 10.84 mL, 62.24 mmol) and 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine (5.314 g, 34.23 mmol) was added and the reaction mixture allowed to warm to ambient temperature over 15 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc. The organic layer was washed water (×2), saturated aqueous NaHCO3 (×2) and brine (×1). The organic layer was dried (MgSO4), filtered and concentrated in vacuo and the residue purified by column chromatography (eluting with 30% EtOAc/petroleum ether) to give the sub-title compound as an off-white solid (8.8 g, 78% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.42 (s, 3H), 3.44 (sept, 1H), 3.67 (s, 3H), 6.95 (br s, 2H), 7.90 (d, 2H), 8.22 (d, 2H) and 8.82 (s, 1H) ppm; (ES+) 366.1.

後処理

  1. temperatureto warm to ambient temperature over 15 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe organic layer was washed water (×2), saturated aqueous NaHCO3 (×2) and brine (×1)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by column chromatography (eluting with 30% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-7f25ef56d2a74701924d7c3c6a0d4728
出典データセット
uspto-grants-2015_06
特許番号
US09062008B2

反応ノート

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