Diisopropylethylamine → 3-Diethylamino-N-{4-[4-(ethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-propionamide

HRID 1927613ノート

反応式

HRID 1927613 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15]([NH:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:26])[CH:3]=1.Cl.[CH2:28]([N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][C:33](O)=[O:34])[CH3:29].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:28]([N:30]([CH2:36][CH3:37])[CH2:31][CH2:32][C:33]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:15](=[O:16])[NH:17][CH2:18][CH3:19])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:10][CH2:9]2)=[C:4]([F:26])[CH:3]=1)=[O:34])[CH3:29]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 3084241N,N-diethyl-beta-alanine hydrochlorideHCID 669319332-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N-ethyl-2-phenyl-acetamide

生成物 1

HCID 166667293-Diethylamino-N-{4-[4-(ethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-propionamide収率 58.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N-ethyl-2-phenyl-acetamide (22 mg, 0.06 mmol), 3-diethylaminopropionic acid hydrochloride (13 mg, 0.07 mmol) and PyBroP (34 mg, 0.07 mmol) in DCM (2 mL) was treated with iPr2NEt (0.032 mL, 0.19 mmol). After 18 h, the mixture was washed with satd. aq. NaHCO3 and brine, dried (MgSO4), and concentrated to give an oil, which was purified by PTLC to give a beige solid (17 mg, 56%). MS (ESI): mass calcd. for C27H38FN5O2, 483.62. m/z found, 484.4 [M+H]+. 1H NMR (CDCl3): 11.15 (s, 1H), 7.38-7.37 (m, 1H), 7.36-7.35 (m, 1H), 7.33-7.32 (m, 3H), 7.31-7.28 (m, 1H), 7.13-7.09 (m, 2H), 6.85 (t, J=9.0, 1H), 3.88 (s, 1H), 3.38-3.33 (m, 2H), 3.06-3.04 (m, 4H), 2.79-2.76 (m, 1H), 2.69-2.65 (m, 4H), 2.59-2.58 (m, 4H), 2.50-2.47 (m, 1H), 1.40-1.38 (m, 1H), 1.35-1.32 (t, J=7.3, 1H), 1.77-1.22 (m, 9H).

後処理

  1. washthe mixture was washed with satd
  2. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil, which
  5. customwas purified by PTLC

出典と根拠

ORDレコード
ord-1753f45cd24843b29b31221035a32012
出典データセット
uspto-grants-2012_05
特許番号
US08183239B2

反応ノート

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