Potassium Carbonate → (3R,5S)-4-(4-benzyl-3,5-dimethyl-piperazin-1-yl)-2-(3,4-dimethoxy-benzyl)-isoindole-1,3-dione

HRID 42323

반응식

HRID 42323 반응식
FC1C=CC=C(F)C=1CN1CC[N:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[C:13](=[O:32])[N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[C:15]3=[O:20])CC1.C(N1CCNCC1)(OC(C)(C)C)=O.F[C:52]1[CH:59]=[CH:58]C=C(F)[C:53]=1[CH2:54]Br.C([O-])([O-])=O.[K+].[K+].[CH3:67][CH2:68][N:69]([CH:73]([CH3:75])[CH3:74])[CH:70]([CH3:72])[CH3:71]>>[CH2:68]([N:69]1[C@@H:73]([CH3:75])[CH2:74][N:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[C:13](=[O:32])[N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[C:15]3=[O:20])[CH2:71][C@H:70]1[CH3:72])[C:67]1[CH:58]=[CH:59][CH:52]=[CH:53][CH:54]=1

참가 물질

6

반응물 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 236276134-(4-(2,6-Difluorobenzyl)piperazin-1-yl)-2-(3,4-dimethoxybenzyl)isoindoline-1,3-dione

생성물 1

HCID 58296018(3R,5S)-4-(4-benzyl-3,5-dimethyl-piperazin-1-yl)-2-(3,4-dimethoxy-benzyl)-isoindole-1,3-dione

실험 절차

Compound 42 was prepared by the methods described in Example 1 for the synthesis of Compound 16, substituting 2,6-dimethylpiperazine (26 mg) for 1-Boc-piperazine in Example 1, Step C; and substituting benzylbromide (0.05 mL) for 2,6-difluorobenzylbromide and K2CO3 (0.09 g) for DIEA in Example1, Step D. Compound 42 was isolated as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.51-7.87 (m, 7 H), 7.10 (d, J=8.2 Hz, 1 H), 6.91-6.94 (m, 2 H), 6.76 (d, J=8.2 Hz, 1H), 4.70 (s, 2 H), 4.62 (s, 2 H), 3.85 (s, 3 H), 3.83 (s, 3 H), 3.71-3.75 (m, 2 H), 3.43-3.52 (m, 4 H), and 1.71 (d, J=5.9 Hz, 6 H); MS (ES+) 500 (M+1); Anal. Calcd for C30H33N3O4.1.67 CF3CO2H.0.3H2O: C, 57.58; H, 5.11; N, 6.04; F, 13.69; H2O, 0.78. Found: C, 57.24; H, 5.08; N, 6.27; F, 13.33; H2O, 0.45.

후처리

  1. customCompound 42 was prepared by the methods

출처 및 근거

ORD 기록
ord-03a5992adee540f787d3c78d5afb2fee
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536174B2

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