Hydrochloric Acid → 1-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-3-carboxylic acid

HRID 216215

반응식

HRID 216215 반응식
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH:3]=1.[NH:21]1[CH2:29][CH2:28][CH2:27][CH:23]([C:24]([OH:26])=[O:25])[CH2:22]1.C([O-])([O-])=O.[K+].[K+].Cl>O.CN1CCCC1=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][NH:10][C:4]1[N:5]=[C:6]([O:8][CH3:9])[N:7]=[C:2]([N:21]2[CH2:29][CH2:28][CH2:27][CH:23]([C:24]([OH:26])=[O:25])[CH2:22]2)[CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 4498Nipecotic AcidHCID 11430Potassium CarbonateHCID 576360046-Chloro-N-[2-(2,4-dichlorophenyl)ethyl]-2-methoxy-4-pyrimidinamine2회

생성물 1

HCID 116690531-{6-[2-(2,4-Dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-3-carboxylic acid수율 47.4%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
140 °C

실험 절차

In a tube is combined (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine [200 mg, 0.6 mmol, Intermediate (44)], nipecotic acid (194 mg, 1.5 mmol), K2CO3 (249 mg, 1.8 mmol) and 1-methyl-2-pyrrolidinone (2.5 mL). The tube is sealed and heated to 140° C. and stirred for hours. The mixture is allowed to cool to ambient temperature, stand for 12 hours, diluted with water (20 mL) and acidified using 3M HCl. A precipitate forms and is collected by filtration and dried under high vacuum to afford 1-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-3-carboxylic acid [121 mg, 47%, Example 73] as a solid. LCMS RT=2.15 minutes, MS: 425 (M+H). IC50=0.8 nM

후처리

  1. customIn a tube is combined
  2. customThe tube is sealed
  3. temperatureto cool to ambient temperature
  4. filtrationA precipitate forms and is collected by filtration
  5. customdried under high vacuum

출처 및 근거

ORD 기록
ord-3b788c77b1ea46e3ae0a76f69167e7f9
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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