4-(1-(4-Bromophenyl)piperidin-4-yl)morpholine → 4-(4-Morpholinopiperidin-1-yl)phenylboronic acid

HRID 447455노트

반응식

HRID 447455 반응식
C(N1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([B:16]([OH:18])[OH:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(C)C.BrC1C=CC(N2CC[CH:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)CC2)=CC=1>>[O:35]1[CH2:36][CH2:37][N:32]([CH:29]2[CH2:5][CH2:6][N:7]([C:10]3[CH:11]=[CH:12][C:13]([B:16]([OH:17])[OH:18])=[CH:14][CH:15]=3)[CH2:8][CH2:9]2)[CH2:33][CH2:34]1

참가 물질

3

반응물 2

HCID 667303494-(1-(4-Bromophenyl)piperidin-4-yl)morpholineHCID 66730443(4-(4-Isopropylpiperazin-1-yl)phenyl)boronic acid

생성물 1

HCID 584862764-(4-Morpholinopiperidin-1-yl)phenylboronic acid수율 40%

실험 절차

The title compound was synthesized according to the synthesis of 4-(4-isopropylpiperazin-1-yl)phenylboronic acid, except substituting 4-(1-(4-bromophenyl)piperidin-4-yl)morpholine (250 mg, 0.77 mmol). The aqueous layer was washed with EtOAc and concentrated. The residue was triturated with THF and the filtrate was concentrated to give the title compound as a yellow solid (87 mg, 40%). 1H NMR (400 MHz, MeOD) δ 7.58 (br s, 2H), 6.93 (d, J=7.5 Hz, 2H), 3.85-3.82 (m, 2H), 3.72 (br s, 4H), 2.72 (t, J=12.3 Hz, 2H), 2.63 (br s, 4H), 2.40-2.34 (m, 1H), 2.01-1.98 (m, 2H), 1.62-1.54 (m, 2H); MS ESI 291.1 [M+H]+, calcd for [C15H23BN2O3+H]+ 291.18.

후처리

  1. customThe title compound was synthesized
  2. washThe aqueous layer was washed with EtOAc
  3. concentrationconcentrated
  4. customThe residue was triturated with THF
  5. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-3c3b6b88c5444628af31c7a065366a1c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481525B2

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