1,1-dimethylethyl 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate → 5-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 2059944ノート

反応式

HRID 2059944 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH2:19][CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH2:19][CH2:20][NH:21][CH2:22]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

参加物

4

反応物 1

HCID 593704861,1-dimethylethyl 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate

生成物 1

HCID 684990255-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride収率 200.7%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

1,1-dimethylethyl 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 3) (2.57 g, 5.47 mmol) was stirred in 4M HCl in 1,4-Dioxane (100 mL). After 1 hour reaction became cloudy and stirring continued for a further 16 hours. Evaporation yielded 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.23 g, 5.49 mmol, 100% yield). 1H NMR (400 MHz, d6-DMSO) δ 9.43 (2H, s), 8.19 (1H, s), 8.11 (1H dd), 8.03-8.00 (1H, m), 7.51-7.45 (3H, m), 4.89 (1H, sept.), 4.38 (2H, s), 3.43 (2H, t), 3.35-3.32 (2H, m), 1.37 (6H, d); m/z (API-ES) 370, 372 [M+H]+.

後処理

  1. customAfter 1 hour reaction
  2. customEvaporation

出典と根拠

ORDレコード
ord-febf293f00bb4896a447ea82020444dd
出典データセット
uspto-grants-2012_10
特許番号
US08278324B2

反応ノート

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