Hydrochloric Acid → [6-(3-Aminomethyl-4-fluoro-phenyl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine hydrochloride

HRID 2110658노트

반응식

HRID 2110658 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:14]=[C:13]([O:28][CH3:29])[N:12]=2)=[CH:7][C:3]=1[CH:4]=[N:5]O.[ClH:30]>C(O)(=O)C.CCOC(C)=O.[Zn]>[ClH:30].[NH2:5][CH2:4][C:3]1[CH:7]=[C:8]([C:11]2[N:12]=[C:13]([O:28][CH3:29])[N:14]=[C:15]([NH:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH:16]=2)[CH:9]=[CH:10][C:2]=1[F:1]

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 730190102-Fluoro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde oxime

생성물 1

HCID 69064976[6-(3-Aminomethyl-4-fluoro-phenyl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine hydrochloride

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-fluoro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde oxime [860 mg, Example 26(a)] in acetic acid (10 mL) is treated with zinc powder (0.6 g, 9.2 mmol). After 1 hour at 20° C., the reaction mixture is filtered through Celite, concentrated, diluted with 1 M sodium hydroxide solution, and extracted with ethyl acetate. The extracts are dried over magnesium sulfate, filtered, and subjected to chromatography on silica gel eluting with 10% MeOH in DCM to provide the free base, which is treated with saturated HCl in EtOAc afford [6-(3-aminomethyl-4-fluoro-phenyl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine hydrochloride [720 mg, Example 27]. LCMS: RT=1.88 minutes, MS: 383 (M+H). IC50=41 nM

후처리

  1. filtrationthe reaction mixture is filtered through Celite
  2. concentrationconcentrated
  3. additiondiluted with 1 M sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customto provide the free base, which

출처 및 근거

ORD 기록
ord-7fdbc424f55548c2ab1177f36f6f4746
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517889B2

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