Triethylamine → 1-[(2-Amino-5-bromo-pyridin-3-ylmethyl)amino]cyclopentanecarboxylic acid methyl ester

HRID 2097057

반응식

HRID 2097057 반응식
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.[CH3:12][O:13][C:14]([C:16]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15].CCN(CC)CC>CN(C=O)C.O>[CH3:12][O:13][C:14]([C:16]1([NH:21][CH2:10][C:5]2[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([Br:2])[CH:4]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 231225Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe)HCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

생성물 1

HCID 592775721-[(2-Amino-5-bromo-pyridin-3-ylmethyl)amino]cyclopentanecarboxylic acid methyl ester수율 43.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To an ice-cold suspension of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (8.64 g, 24.9 mmol) and 1-amino-cyclopentanecarboxylic acid methyl ester (3.56 g, 24.9 mmol) in DMF (100 mL) was added Et3N (5.30 mL, 37.4 mmol) slowly. The mixture was stirred for 2 h and then diluted with H2O. The solid was collected by filtration to give the title compound (3.55 g, 43%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.02 (d, J=2.3 Hz, 1H), 7.37 (d, J=2.3 Hz, 1H), 5.49 (s, 2H), 3.76 (s, 3H), 3.52 (s, 2H), 2.12-2.05 (m, 2H), 1.79 (br s, 7H).

후처리

  1. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-7c00f62d27aa4d579cdfa18da41f79dd
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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