Diisopropylethylamine → 2-Methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzofuran-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)amide

HRID 1825196ノート

反応式

HRID 1825196 の反応式
[CH3:1][C:2]1[O:3][C:4]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[CH:22][S:23][C:16]=34)[CH:11]=[CH:10][C:5]=2[C:6]=1[C:7]([OH:9])=O.[N:24]1([C:30]2[N:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[N:24]1([C:30]2[N:35]=[CH:34][C:33]([NH:36][C:7]([C:6]3[C:5]4[CH:10]=[CH:11][C:12]([O:14][C:15]5[CH:20]=[CH:19][N:18]=[C:17]6[CH:21]=[CH:22][S:23][C:16]=56)=[CH:13][C:4]=4[O:3][C:2]=3[CH3:1])=[O:9])=[CH:32][CH:31]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 1040596-(Morpholino)pyridin-3-amineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 221435102-Methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carboxylic acid

生成物 1

HCID 207678132-Methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzofuran-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carboxylic acid 100 (70 mg, 0.215 mmole), 6-Morpholin-4-yl-pyridin-3-ylamine (77 mg, 0.43 mmole), HATU (163 mg, 0.43 mmole), and diisopropylethylamine (75 μl, 0.43 mmole) were stirred in DMF (2 ml) at ambient temperature for 17 hr. The mixture was then added dropwise to a solution of cold aqueous NaHCO3 resulting in a precipitate which was collected by filtration. This material was purified on silica gel using a gradient of 0 to 5% methanol in a 1:1 mixture of ethyl acetate and dichloromethane as eluent to give 77 mg (74%) of a lavander solid. 1H NMR (CD3CN) δ 8.50 (1H, d, J=5.3 Hz), 8.37 (1H, d, J=2.5 Hz), 8.29 (1H, s), 7.92–7.88 (3H, m), 7.54 (1H, d, J=5.3 Hz), 7.45 (1H, d, J=2.0 Hz), 7.23 (1H, dd, J=8.6, 2.0 Hz), 6.78 (1H, d, J=9.1 Hz), 6.64 (1H, d, J=5.3 Hz), 3.76 (4H, t, J=4.9 Hz), 3.44 (4H, t, J=4.9 Hz), 2.72 (3H, s).

後処理

  1. filtrationwas collected by filtration
  2. customThis material was purified on silica gel using a gradient of 0 to 5% methanol
  3. additionin a 1:1 mixture of ethyl acetate and dichloromethane as eluent
  4. customto give 77 mg (74%) of a lavander solid

出典と根拠

ORDレコード
ord-4bec61ebdb7d42338420fd93822dffb0
出典データセット
uspto-grants-2006_05
特許番号
US07045528B2

反応ノート

読み込み中…