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 1047047ノート

反応式

HRID 1047047 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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].

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-d1c46b0441a647b38c0f1e58d540a4e3
出典データセット
uspto-grants-2013_10
特許番号
US08569331B2

反応ノート

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