1,4-Dioxane hydrochloride → 1-{4-[2-(3-Nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochloride

HRID 1047046

反応式

HRID 1047046 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3([NH:38]C(=O)OC(C)(C)C)[CH2:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[ClH:46].O1CCOCC1>C(Cl)Cl>[ClH:46].[ClH:46].[ClH:46].[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:29]=[CH:30][C:31]([C:34]3([NH2:38])[CH2:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

4

反応物 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087657tert-Butyl (1-{4-[2-(3-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate

生成物 1

HCID 675041811-{4-[2-(3-Nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochloride収率 71.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl (1-{4-[2-(3-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (30.0 mg, 0.0499 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 18 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (21.7 mg, 71.3%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.69 (br s, 2H), 8.64 (s, 1H), 8.23 (t, J=1.8 Hz, 1H), 8.14-8.08 (m, 2H), 8.00 (dd, J=8.0, 1.8 Hz, 1H), 7.93-7.88 (m, 1H), 7.64-7.57 (m, 3H), 7.44-7.36 (m, 3H), 7.34-7.29 (m, 1H), 7.18-7.12 (m, 1H), 6.98 (dd, J=8.0, 1.8 Hz, 1H), 6.75 (dd, J=8.0, 4.8 Hz, 1H), 2.65-2.46 (m, 4H), 2.26-2.12 (m, 1H), 1.93-1.78 (m, 1H); LCMS: 501 [M+H].

後処理

  1. concentrationThe mixture was concentrated
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with ether

出典と根拠

ORDレコード
ord-dec97d2de4b24da5949639ff58104663
出典データセット
uspto-grants-2013_10
特許番号
US08569331B2

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