Dimethylformamide → cis-N-[1-[3-(4-Fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

HRID 935

반응식

HRID 935 반응식
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C:10](=[O:25])[C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([NH2:18])=[CH:13][C:12]=2[O:19][C@@H:20]([CH3:24])[C:21]#[C:22][CH3:23])[CH2:7][CH2:6][NH:5][CH2:4]1.[F:26][C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH2:33][CH2:34]Br)=[CH:29][CH:28]=1.C(N(CC)CC)C.CN(C=O)C>C(OCC)(=O)C>[F:26][C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH2:33][CH2:34][N:5]2[CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:25])[C:11]3[CH:16]=[C:15]([Cl:17])[C:14]([NH2:18])=[CH:13][C:12]=3[O:19][C@@H:20]([CH3:24])[C:21]#[C:22][CH3:23])[C@H:3]([O:2][CH3:1])[CH2:4]2)=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2600041-(3-Bromopropoxy)-4-fluorobenzeneHCID 69232145cis-N-(3-Methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

생성물 1

HCID 69229498cis-N-[1-[3-(4-Fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide수율 91.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A mixture comprising 0.10 g of the cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide, 0.07 g of 3-(4-fluorophenoxy)propyl bromide, 0.20 g of triethylamine and 10 ml of DMF was stirred at 50° C. for 2 hours and cooled. Ethyl acetate was poured into the resulting mixture. The obtained mixture was washed with water thrice, dried over magnesium sulfate, and freed from the solvent. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane) to give 0.13 g of the title compound.

후처리

  1. temperaturecooled
  2. washThe obtained mixture was washed with water thrice
  3. dry with materialdried over magnesium sulfate
  4. customThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-e90e3b33efd8427982a8d67e8d113a2f
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723472

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