Pentanoyl chloride, 4-methyl- → {4-[2-Fluoro-4-(4-methyl-pentanoylamino)-phenyl]-piperazin-1-yl}-phenyl-acetic acid methyl ester

HRID 1927611

반응식

HRID 1927611 반응식
[CH3:1][O:2][C:3](=[O:25])[CH:4]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=2[F:24])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:26][CH:27]([CH3:33])[CH2:28][CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:25])[CH:4]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:30](=[O:31])[CH2:29][CH2:28][CH:27]([CH3:33])[CH3:26])=[CH:19][C:18]=2[F:24])[CH2:15][CH2:16]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

4

반응물 2

HCID 170008Pentanoyl chloride, 4-methyl-HCID 69304062[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester

생성물 1

HCID 58870708{4-[2-Fluoro-4-(4-methyl-pentanoylamino)-phenyl]-piperazin-1-yl}-phenyl-acetic acid methyl ester수율 74.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of [4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester (35 mg, 0.10 mmol) in DCM (2 mL) was treated with 4-methylvaleroyl chloride (15 mg, 0.11 mmol) followed by TEA (16 μL, 0.11 mmol). After 16 h, the mixture was purified directly by PTLC to give a beige solid (33 mg, 73%). MS (ESI): mass calcd. for C25H32FN3O3, 441.55; m/z found, 442.5 [M+H]+. 1H NMR (CDCl3): 7.46-7.44 (m, 2H), 7.42-7.39 (m, 1H), 7.36-7.32 (m, 3H), 7.05-7.03 (m, 1H), 6.98 (br s, 1H), 6.88-6.84 (m, 1H), 4.06 (s, 1H), 3.70 (s, 3H), 3.10-3.06 (m, 4H), 2.34-2.31 (m, 4H), 2.35-2.31 (m, 2H), 1.62-1.60 (m, 3H), 0.92 (d, J=6.1, 6H).

후처리

  1. customthe mixture was purified directly by PTLC

출처 및 근거

ORD 기록
ord-def361627ca244eeb3f9c0b702e4c970
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183239B2

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