Water → [2-(4-Amino-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine

HRID 626769노트

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HRID 626769 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[N:12]1[CH:29]=[C:15]2[C:16]([NH:21][C:22]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=3)=[N:17][CH:18]=[C:19]([F:20])[C:14]2=[N:13]1.C1COCC1.O.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[C:4]([Cl:11])[C:3]([N:12]2[CH:29]=[C:15]3[C:16]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:17][CH:18]=[C:19]([F:20])[C:14]3=[N:13]2)=[C:2]([Cl:1])[CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium Chloride2회HCID 69671549[2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine

생성물 1

HCID 69671162[2-(4-Amino-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine수율 74.2%

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 702Ethanol용매

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온도
70 °C

실험 절차

[2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine (173 mg, 0.40 mmol) was dissolved in ethanol (10 mL) and THF (4.0 mL) and water (1.0 mL) were added, followed by iron powder (325 mesh, 112 mg, 2.0 mmol) and ammonium chloride (86 mg, 1.6 mmol). The reaction mixture was heated at 70° C. for 4 hours. More iron powder (112 mg) and ammonium chloride (100 mg) were added and the mixture was heated at 70° C. for another 5 hours. The resultant mixture was cooled and filtered through Celite®. The filtrate was concentrated under reduced pressure and the residue was triturated with water. The solid obtained was dried under reduced pressure and purified by silica gel flash chromatography (0-5% methanol in DCM) to afford the title compound as an off-white solid (120 mg, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.62 (s, 1H), 9.13 (d, J=2.6 Hz, 1H), 8.71 (d, J=1.2 Hz, 1H), 8.42 (s, 1H), 7.96 (d, J=3.5 Hz, 1H), 6.83 (s, 2H), 6.30 (s, 2H), 2.46 (s, 3H). LCMS (Method B): RT=3.00 min, m/z: 404 [M+H+].

후처리

  1. temperaturethe mixture was heated at 70° C. for another 5 hours
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was triturated with water
  5. customThe solid obtained
  6. customwas dried under reduced pressure
  7. custompurified by silica gel flash chromatography (0-5% methanol in DCM)

출처 및 근거

ORD 기록
ord-6fb36469282d48c78272d0eb0c92df79
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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