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p-Toluenesulfonic acid monohydrate → Ammonia methanol

HRID 710224
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HRID 710224 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH3:17])[C:11]([CH3:19])([CH3:18])[CH2:10]2)[C:5]([C:20]#[N:21])=[CH:4][N:3]=1.[CH:22]1([C:25]2[C:30]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:29][C:28]([NH2:36])=[C:27]([F:37])[CH:26]=2)[CH2:24][CH2:23]1.[OH2:38].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C>[NH3:3].[CH3:2][OH:38].[CH3:17][N:12]1[C:13]([CH3:16])([CH3:15])[CH2:14][CH:9]([NH:8][C:6]2[C:5]([C:20]#[N:21])=[CH:4][N:3]=[C:2]([NH:36][C:28]3[CH:29]=[C:30]([N:31]4[CH:35]=[N:34][N:33]=[N:32]4)[C:25]([CH:22]4[CH2:23][CH2:24]4)=[CH:26][C:27]=3[F:37])[N:7]=2)[CH2:10][C:11]1([CH3:19])[CH3:18]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58065786HCID 58065786, 화합물HCID 86661500HCID 86661500, 화합물

생성물 2

HCID 21705897Ammonia methanol수율 2%HCID 66684470HCID 66684470, 화합물

시약·촉매·용매 1

HCID 3776Isopropanol
용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-chloro-5-cyano-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidin-4-amine (0.205 g, 0.66 mmol, 1 equiv), 4-cyclopropyl-2-fluoro-5-(1H-tetrazol-1-yl)benzenamine (0.160 g, 0.730 mmol, 1.1 equiv), and para-toluenesulfonic acid monohydrate (0.100 g, 0.530 mmol, 0.8 equiv) in IPA (25 mL) were heated to 100° C. overnight. After cooling to ambient temperature, the crude mixture was quenched with 2M NH3/MeOH followed by concentrating to dryness and repeating once. The crude product was purified by flash chromatography and eluted with DCM:2M NH3/MeOH (100:0 to 95:5 using 2% 2M NH3/MeOH increments) to provide the desired product which was recrystallized with DCM/Hexanes to give the title compound (0.170 mg, 52%) as a solid.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customthe crude mixture was quenched with 2M NH3/MeOH
  3. concentrationby concentrating to dryness
  4. customThe crude product was purified by flash chromatography
  5. washeluted with DCM

출처 및 근거

ORD 기록
ord-e3e351d68cb34073bd56379b7d8f58a9
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181222B2

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