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

반응식

HRID 1047046 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-dec97d2de4b24da5949639ff58104663
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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