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N-methyl-2-pyrrolidone → 4-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzoic acid hydrochloride

HRID 1786940
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HRID 1786940 반응식
Cl.[Cl:2][C:3]1[C:4]2[NH:11][C:10]([C:12]3[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=3)=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH3:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1)[NH2:27].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>C(OCC)(=O)C.O>[ClH:2].[CH3:23][C:24]1[CH:25]=[C:26]([NH:27][C:3]2[C:4]3[NH:11][C:10]([C:12]4[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:21][CH:22]=4)=[CH:9][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1
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참가 물질

7

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineHCID 86615760ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride

생성물 1

HCID 675204054-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzoic acid hydrochloride수율 57.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

A mixture of ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride (1.297 g), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (1.00 g), diisopropylethylamine (0.834 g) and 1-methyl-2-pyrrolidinone (12.5 mL) was stirred at 140° C. for 3 hrs, poured into water (100 mL)-ethyl acetate (150 mL) and the precipitated solid was collected by filtration. The solid washed with ethyl acetate and dried under reduced pressure at 60° C. The obtained solid was suspended in methanol (40 mL), and 1N aqueous sodium hydroxide solution (20 mL) was added. After stirring at room temperature for 12 hrs, the solvent was evaporated under reduced pressure, and the residue was adjusted to pH 2 with 1N hydrochloric acid. The precipitated solid was collected by filtration, washed with water and dried under reduced pressure at 60° C. to give the title compound (1.08 g).

후처리

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe solid washed with ethyl acetate
  3. customdried under reduced pressure at 60° C
  4. addition1N aqueous sodium hydroxide solution (20 mL) was added
  5. stirringAfter stirring at room temperature for 12 hrs
  6. customthe solvent was evaporated under reduced pressure
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure at 60° C.

출처 및 근거

ORD 기록
ord-e690e0d37b5647b480ee3cba21bcd7dd
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07507740B2

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