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Hydrochloric Acid → HCID 178432624、化合物

HRID 2377979
ノート
印刷プレビュー

反応式

HRID 2377979 の反応式
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:11][C:12]([C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])=[C:13]([CH3:15])[N:14]=1.Cl.C(N(CC)CC)C.[NH2:32][CH2:33][C@H:34]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=1)[OH:35]>C(O)(=O)C>[Cl:42][C:38]1[CH:37]=[C:36]([C@H:34]([OH:35])[CH2:33][NH:32][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:10]2[NH:11][C:12]([C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:41]=[CH:40][CH:39]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 8471TriethylamineHCID 9855591(S)-2-amino-1-(3-chlorophenyl)ethanolHCID 178494188HCID 178494188、化合物

生成物 1

HCID 178432624HCID 178432624、化合物収率 25.7%

試薬・触媒・溶媒 1

HCID 176Acetic Acid
溶媒

反応条件

温度
90 °C

実験手順

(2-(4-Iodo-2-methoxypyridin-3-yl)-4-methyl-1H-imidazol-5-yl)(morpholino)methanone (0.007 g, 0.017 mmol) was dissolved in acetic acid (1 mL) and concentrated hydrochloric acid (1 mL) and this mixture was stirred at 100° C. for 1 hour. The mixture was then evaporated and the residue was dissolved in N,N-dimethylformamide (2 mL) and treated with triethylamine (100 μL, 0.72 mmol) and the hydrochloric acid salt of (S)-2-amino-1-[3-chlorophenyl]ethanol (0.010 g, 0.048 mmol). The mixture was heated at 90° C. for 4 hours, then the solvent was evaporated and the residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water) to give the title compound (0.002 g, 25%) as a white solid. HPLC 100% (220 nm), LCMS (+ESI, M+H+) m/z 458; 1H NMR (400 MHz, methanol-d4) δ (ppm): 2.37 (3H, s), 3.45-4.0 (10H, m), 4.7-4.9 (1H, m, overlapped by D2O), 6.10 (1H, d, J=7.8 Hz), 7.10 (1H, d, J=7.6 Hz), 7.14-7.24 (3H, m), 7.36 (1H, s), 10.26 (1H, br s).

後処理

  1. customThe mixture was then evaporated
  2. dissolutionthe residue was dissolved in N,N-dimethylformamide (2 mL)
  3. customthe solvent was evaporated
  4. customthe residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water)

出典と根拠

ORDレコード
ord-2cdc9b6f03c6489ea133cd53c42cfb87
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07470713B2

反応ノート

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