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

HRID 1825196노트

반응식

HRID 1825196 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4bec61ebdb7d42338420fd93822dffb0
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045528B2

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