tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(2-{[5-chloro-2-(trifluoromethyl)benzyl]sulfonyl}thieno[3,2-c]pyridin-4-yl)piperazine-1-carboxylate

HRID 549298

反応式

HRID 549298 の反応式
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+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:24]([F:27])([F:26])[F:25])=[C:20]([CH:23]=1)[CH2:21]Br.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C(#N)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:24]([F:27])([F:26])[F:25])=[C:20]([CH:23]=1)[CH2:21][S:11]([C:9]1[S:10][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:38]3[CH2:37][CH2:36][N:35]([C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH2:40][CH2:39]3)[C:7]=2[CH:8]=1)(=[O:13])=[O:12]

参加物

5

反応物 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27781162-(Bromomethyl)-4-chloro-1-(trifluoromethyl)benzeneHCID 86591057Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate

生成物 1

HCID 67157405tert-Butyl 4-(2-{[5-chloro-2-(trifluoromethyl)benzyl]sulfonyl}thieno[3,2-c]pyridin-4-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 5-chloro-2-(trifluoromethyl)benzylbromide (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 0.019 g (7.5% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.12-8.14 (m, 1H), 7.80-7.88 (m, 2H), 7.47-7.66 (m, 2H), 4.71 (s, 2H), 3.74-3.83 (m, 4H), 3.63-3.72 (m, 4H), 1.49 (s, 9H); MS (ESI+) for C24H25ClF3N3O4S2 m/z 576 (M+H)+. HPLC 74%, RT 2.30 min (YMC ODS AQ, 33×3 mm, 10-90% acetonitrile in 3 min).

出典と根拠

ORDレコード
ord-4689135fec7b473b9a7e7d266e0cae6e
出典データセット
uspto-grants-2011_05
特許番号
US07943639B2

関連ノート

読み込み中…