Hydrochloric Acid → HCID 86600351、化合物

HRID 713735ノート

反応式

HRID 713735 の反応式
[CH3:1][N:2]([CH3:28])[C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:12]([NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=1)=[O:13].[NH2:29][OH:30].[OH-].[Na+].Cl>CO.C1COCC1>[OH:30][NH:29][C:22](=[O:24])[C:21]1[CH:26]=[CH:27][C:18]([O:17][CH2:16][CH2:15][NH:14][C:12]([C:4]2[O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:3]=2[N:2]([CH3:1])[CH3:28])=[O:13])=[CH:19][CH:20]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 66688396Methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate

生成物 1

HCID 86600351HCID 86600351、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of crude methyl 4-[2-(3-dimethylaminobenzofuran-2-yl-carbonylamino)-ethoxy]-benzoate in MeOH and THF was added excess aqueous hydroxylamine solution and NaOH(aq.) to give pH 10-11. The reaction mixture was stirred overnight and then neutralized to pH 7-8 with aqueous hydrochloric acid and concentrated in vacuo. The residue was dissolved in acetonitrile and water and purified with prep HPLC to give the title compound (107 mg). 1H NMR (400 MHz, DMSO-d6) δ 9.88 (m, 1H), 9.31 (t, J=6.0 Hz, 1H), 8.04 (d, J=7.6 Hz, 1H), 7.70 (m, 3H), 7.57 (t, J=7.6 Hz, 1H), 7.45 (t, J=7.6 Hz, 1H), 6.99 (d, J=9.2 Hz, 2H), 4.76 (d, J=4.8 Hz, 2H), 4.23 (t, J=6.0 Hz, 2H), 3.71 (m, 2H), 2.84 (s, 3H), 2.83 (s, 3H). EM (calc.): 397.2; MS (ESI) m/e (M+1H)+: 398.1, (M−1H)−: 396.2.

後処理

  1. customto give pH 10-11
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in acetonitrile
  4. customwater and purified with prep HPLC

出典と根拠

ORDレコード
ord-a7fa3159356b43be9cb2abbbd569dca7
出典データセット
uspto-grants-2015_11
特許番号
US09186347B1

反応ノート

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