1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68651900、化合物

HRID 646775ノート

反応式

HRID 646775 の反応式
[NH2:1][C:2]1[C:3]([C:26](O)=[O:27])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][C@H:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)=[O:15])[CH:9]=2)=[CH:6][N:7]=1.[NH:29]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]([NH2:36])[CH2:30]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>>[NH2:1][C:2]1[C:3]([C:26]([NH:36][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][NH:29][CH2:30]2)=[O:27])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][C@@H:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]3)=[O:15])[CH:9]=2)=[CH:6][N:7]=1

参加物

5

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2756445Azepan-3-amineHCID 68651967HCID 68651967、化合物

生成物 1

HCID 68651900HCID 68651900、化合物収率 4.3%

実験手順

To a solution of 3-amino-6-(3-{[(1R)-2,3-dihydro-1H-inden-1-ylamino]carbonyl}phenyl)pyrazine-2-carboxylic acid (409 mg, 1.09 mmol) were added azepan-3-amine (125 mg, 1.09 mmol), EDCI (252 mg, 1.31 mmol), HOBt (178 mg, 1.31 mmol) at ambient temperature. After being stirred for 2 h, the reaction mixture was quenched by addition of aqueous sodium bicarbonate followed by extraction with ethyl acetate (20 mL×3). The aqueous phase was extracted once with additional ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride then dried over anhydrous magnesium sulfate. Filtration and concentration in vacuo gave a crude oil, which was purified by preparative HPLC to yield the 3-amino-N-azepan-3-yl-6-(3-{[(1S)-2,3-dihydro-1H-inden-1-ylamino]carbonyl}phenyl)pyrazine-2-carboxamide (22 mg, 4.2% yield): 1H NMR (400 MHz, CD3OD): δ 8.70 (m, 1H), 8.67 (m, 1H), 8.27 (m, 1H) 7.97 (m, 1H), 7.62 (t, 1H), 7.25 (m, 4H), 5.70 (m, 1H), 4.99 (m, 1H), 4.43 (m, 1H), 3.46 (m, 2H), 3.38 (m, 1H), 3.15 (m, 2H), 2.94 (m, 1H), 2.61 (m, 1H), 2.17 (m, 2H), 1.95 (m, 4H), 1.62 (m, 1H); MS (EI) for C27H30N6O2: 471.32 (MH+).

後処理

  1. customthe reaction mixture was quenched by addition of aqueous sodium bicarbonate
  2. extractionfollowed by extraction with ethyl acetate (20 mL×3)
  3. extractionThe aqueous phase was extracted once with additional ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialthen dried over anhydrous magnesium sulfate
  6. filtrationFiltration and concentration in vacuo
  7. customgave a crude oil, which
  8. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-0f1e8f1993dd4266803c786a120fdeb4
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

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