Water → HCID 178485544, 화합물

HRID 1014508노트

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HRID 1014508 반응식
[CH3:1][N:2]([CH3:50])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:48][CH3:49])=[C:12]([NH:15][C:16]3[N:17]=[C:18]([NH:35][C:36]4[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[C:37]=4[C:38]([NH:40][CH3:41])=[O:39])[C:19]4[CH:24]=[CH:23][N:22](S(C5C=CC(C)=CC=5)(=O)=O)[C:20]=4[N:21]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5].[OH-].[Na+].O>O1CCOCC1.CCOC(C)=O.C1COCC1>[CH3:50][N:2]([CH3:1])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:48][CH3:49])=[C:12]([NH:15][C:16]3[NH:21][C:20]4=[N:22][CH:23]=[CH:24][C:19]4=[C:18]([NH:35][C:36]4[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[C:37]=4[C:38]([NH:40][CH3:41])=[O:39])[N:17]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5]

참가 물질

7

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 673165062-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4,6-difluoro-N-methylbenzamide

생성물 1

HCID 178485544HCID 178485544, 화합물수율 90.3%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

To a suspension of 2-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4,6-difluoro-N-methylbenzamide (0.950 g, 1.07 mmol) in 1,4 dioxane (10 mL) in a microwave vessel was added 6 N NaOH (10 ml) and water (3 mL). The resulting mixture was stirred in the microwave at 120° C. for 9 min. The reaction mixture was diluted with EtOAc and THF and the organic layer was washed with water and a saturated brine solution. Combined organic layers were dried over sodium sulfate and all solvents were removed under reduced pressure and purified via chromatography on SiO2 to afford 2-[(2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-4,6-difluoro-N-methylbenzamide (0.532 g, 0.966 mmol) as a beige solid. (ESIMS (M+H)+=551). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.23 (s, 6 H) 2.83 (d, J=4.40 Hz, 3 H) 3.06-3.12 (m, 2 H) 3.33 (s, 2 H) 3.76 (s, 2 H) 4.05-4.23 (m, 2 H) 6.25 (dd, J=3.39, 1.74 Hz, 1 H) 6.80-6.94 (m, 1 H) 6.93-7.04 (m, 2 H) 7.80 (s, 1 H) 8.41-8.54 (m, 2 H) 8.54-8.64 (m, 1 H) 10.79 (s, 1 H) 11.33 (br. s., 1 H)

후처리

  1. washthe organic layer was washed with water
  2. dry with materialCombined organic layers were dried over sodium sulfate
  3. customall solvents were removed under reduced pressure
  4. custompurified via chromatography on SiO2

출처 및 근거

ORD 기록
ord-e4c3b37afb8c4edc976bd158fd22e320
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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