2-Bromobenzyl bromide → 6-[3(R)-Amino-piperidin-1-yl]-1-(2-bromo-benzyl)-1H-pyrimidine-2,4-dione

HRID 1515150노트

반응식

HRID 1515150 반응식
ClC1N(CC2C=CC=CC=2C#N)C(=O)NC(=O)C=1.[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br.[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]2[N:40](CC3C=CC=CC=3C#N)[C:39](=[O:50])[N:38](C)[C:37](=[O:52])[CH:36]=2)[CH2:30]1>>[NH2:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][N:31]([C:35]2[N:40]([CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[Br:19])[C:39](=[O:50])[NH:38][C:37](=[O:52])[CH:36]=2)[CH2:30]1

참가 물질

4

반응물 3

HCID 769652-Bromobenzyl bromideHCID 113574682-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrileHCID 11450633Alogliptin

생성물 1

HCID 112919016-[3(R)-Amino-piperidin-1-yl]-1-(2-bromo-benzyl)-1H-pyrimidine-2,4-dione

실험 절차

The title compound was prepared in two steps. The first step was accomplished using the procedure for the preparation of compound 2, except that 2-bromobenzylbromide was used in the place of α-Bromo-o-tolunitrile. The crude product was then converted to the title compound by the method used in the preparation of compound 4. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1): δ 7.52 (d, J=8.1 Hz, 1 H), 7.24 (t, J=7.8 Hz, 1 H), 7.10 (t, J=7.8 Hz, 1 H), 6.89 (d, J=7.579 Hz, 1 H), 5.27 (s, 1 H), 4.92-5.04 (ABq, J=34.1, 15.0 Hz, 2 H), 3.27 (bd, J=10.4 Hz, 1 H), 3.09-3.18 (m, 1 H), 2.89 (m, 1 H), 2.70 (t, J=10.9 Hz, 1 H), 2.48 (t, J=12.0 Hz, 1 H), 2.03 (m, 1 H), 1.60-1.71 (m, 1 H), 1.42-1.53 (m, 2 H). MS (ES) [m+H] calc'd for C16H20BrN4O2, 379.1; found, 379.1.

후처리

  1. customThe title compound was prepared in two steps

출처 및 근거

ORD 기록
ord-5ba3e46a2da142d6afedf9d2107c0106
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222411B2

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