p-Xylyl bromide → tert-Butyl 4-{2-[(4-methylbenzyl)sulfonyl]thieno[3,2-c]pyridin-4-yl}piperazine-1-carboxylate

HRID 549297

반응식

HRID 549297 반응식
Cl[C:2]1[C:7]2[CH:8]=[C:9]([S:11]([O-:13])=[O:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[Li+].[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(#N)C>[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:11]([C:9]2[S:10][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([N:34]4[CH2:33][CH2:32][N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:36][CH2:35]4)[C:7]=3[CH:8]=2)(=[O:13])=[O:12])=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 7721p-Xylyl bromideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86591057Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate

생성물 1

HCID 67157698tert-Butyl 4-{2-[(4-methylbenzyl)sulfonyl]thieno[3,2-c]pyridin-4-yl}piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 4-methylbenzylbromide (0.59 mmol) as described in Method P above and then reacted further with tert-butyl-piperazine-1-carboxylate as described in Method Q. Yield 0.005 g (3% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=6 Hz 1H), 7.40 (s, 1H), 7.00-7.16 (m, 4H), 4.42 (s, 2H), 3.46-3.60 (m, 4H), 3.37-3.46 (m, 4H), 2.34 (s, 3H), 1.49 (s, 9H); MS (ESI+) for C24H29N3O4S2 m/z 488 (M+H)+. HPLC 69%, RT 2.06 min (YMC ODS AQ, 33×3 mm, 10-90% acetonitrile in 3 min).

출처 및 근거

ORD 기록
ord-4e7c302031e749d89adc52174c760092
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943639B2

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