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

HRID 1047047노트

반응식

HRID 1047047 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]4[N:21]=[CH:22][CH:23]=[CH:24][C:12]=4[N:11]3[C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)[CH:5]=[CH:6][CH:7]=1.[ClH:44].O1CCOCC1>C(Cl)Cl>[ClH:44].[ClH:44].[ClH:44].[ClH:44].[NH2:36][C:32]1([C:29]2[CH:28]=[CH:27][C:26]([C:25]3[N:11]4[C:12]5[CH:24]=[CH:23][CH:22]=[N:21][C:13]=5[NH:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=5[C:10]4=[N:9][C:8]=3[C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=3)[NH2:1])=[CH:31][CH:30]=2)[CH2:33][CH2:34][CH2:35]1

참가 물질

4

반응물 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087660tert-Butyl (1-{4-[2-(3-aminophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate

생성물 1

HCID 675039013-{3-[4-(1-Aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}aniline tetrahydrochloride수율 83.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl (1-{4-[2-(3-aminophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (40.0 mg, 0.0701 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 15.5 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (36.2 mg, 83.8%) as pale red solid. 1H-NMR (DMSO-d6) 400 MHz δ: 8.78 (br s, 2H), 8.63 (s, 1H), 8.11 (dd, J=4.8, 1.6 Hz, 1H), 7.96-7.92 (m, 1H), 7.60-7.48 (m, 3H), 7.42-7.09 (m, 8H), 6.93 (dd, J=8.2, 1.4 Hz, 1H), 6.75 (dd, J=7.8, 4.6 Hz, 1H), 2.65-2.48 (m, 4H), 2.27-2.13 (m, 1H), 1.90-1.76 (m, 1H); LCMS: 471 [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-d1c46b0441a647b38c0f1e58d540a4e3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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