1-(4-Bromophenyl)-cis-3,5-dimethylpiperazine → 4-(cis-3,5-Dimethylpiperazin-1-yl)phenylboronic acid

HRID 447318노트

반응식

HRID 447318 반응식
C(N1CCN(C2C=CC([B:16]([OH:18])[OH:17])=CC=2)CC1)(C)C.Br[C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][C@H:30]([CH3:32])[NH:29][C@H:28]([CH3:33])[CH2:27]2)=[CH:22][CH:21]=1>>[CH3:33][C@H:28]1[NH:29][C@@H:30]([CH3:32])[CH2:31][N:26]([C:23]2[CH:24]=[CH:25][C:20]([B:16]([OH:18])[OH:17])=[CH:21][CH:22]=2)[CH2:27]1

참가 물질

3

반응물 2

HCID 667303611-(4-Bromophenyl)-cis-3,5-dimethylpiperazineHCID 66730443(4-(4-Isopropylpiperazin-1-yl)phenyl)boronic acid

생성물 1

HCID 584863454-(cis-3,5-Dimethylpiperazin-1-yl)phenylboronic acid

실험 절차

The title compound was synthesized according to the synthesis of 4-(4-isopropylpiperazin-1-yl)phenylboronic acid, except substituting 1-(4-bromophenyl)-cis-3,5-dimethylpiperazine (300 mg, 1.11 mmol). The reaction was quenched with sat. NH4Cl solution, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to dryness. The title compound was isolated by silica gel chromatography (MeOH/CH2Cl2, 6:94 to 1:4) as a yellow solid (59 mg, 23%). 1H NMR (400 MHz, MeOD) δ 7.59 (d, J=6.2 Hz, 2H), 6.91 (d, J=8.2 Hz, 2H), 3.67-3.63 (m, 2H), 3.09-3.01 (m, 2H), 2.32 (t, J=11.6 Hz, 2H), 1.18 (d, J=6.4 Hz, 6H); MS ESI 235.1 [M+H]+, calcd for [C12H19BN2O2+H]+ 235.15.

후처리

  1. customThe title compound was synthesized
  2. customThe reaction was quenched with sat. NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-0b47c1e668874f6f8689e740880ef5e7
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481533B2

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