Diisopropylethylamine → HCID 24900572、化合物

HRID 709593ノート

反応式

HRID 709593 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][C:10]([OH:12])=O)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:37][C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[NH:46][CH2:45][CH2:44][CH2:43]2.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][C:10]([N:46]2[C:47]3[C:42](=[CH:41][CH:40]=[CH:39][C:38]=3[CH3:37])[CH2:43][CH2:44][CH2:45]2)=[O:12])=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 27741668-Methyl-1,2,3,4-tetrahydroquinolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24694245HCID 24694245、化合物

生成物 1

HCID 24900572HCID 24900572、化合物収率 20%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (5-chloro-pyridin-2-ylsulfanyl)-acetic acid (15, 0.27 g, 1.3 mmol) in dry CH2Cl2 (10 mL) and DMF (2 mL) at 0° C. was added HATU (0.5 g, 1.3 mmol) and reaction mixture was stirred for 30 min at ambient temperature. Then the reaction mixture was cooled to 0° C. and neat 8-methyl-1,2,3,4-tetrahydroquinolin (0.20 g, 1.3 mmol) was added via syringe followed by addition of DIPEA, (0.69 mL, 3.9 mmol). The reaction mixture was allowed to warm to room temperature over 18 h. The reaction mixture was diluted with 50 mL of CH2Cl2, washed with H2O, 10% citric acid, NaHCO3 (saturated), brine, dried over Na2SO4 and concentrated. The crude was purified by column chromatography (hexanes/EtOAc) to give 90 mg of the target 16 as a white solid in 20% yield. MS (APCI) m/z: 333.1 (100%, [M+H]+, 186.0 (20%, [M−147+H]+; HPLC purity: 100%; Anal. Calcd. for C17H17ClN2OS: C, 61.34; H, 5.15; N, 8.42; Cl, 10.65; S, 9.63. Found: C, 61.33; H, 5.06; N, 8.36; Cl. 10.67; S, 9.56.

後処理

  1. temperatureThen the reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature over 18 h
  3. washwashed with H2O, 10% citric acid, NaHCO3 (saturated), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by column chromatography (hexanes/EtOAc)

出典と根拠

ORDレコード
ord-4c5491ff899f46048b528f6a1f0e8ea5
出典データセット
uspto-grants-2015_11
特許番号
US09181219B2

反応ノート

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