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

HRID 1047069노트

반응식

HRID 1047069 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]3[N:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]2[C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([C:34]2([NH:38]C(=O)OC(C)(C)C)[CH2:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1.[ClH:46].O1CCOCC1>C(Cl)Cl>[ClH:46].[ClH:46].[ClH:46].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]3[N:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]2[C:27]=1[C:28]1[CH:29]=[CH:30][C:31]([C:34]2([NH2:38])[CH2:37][CH2:36][CH2:35]2)=[CH:32][CH:33]=1

참가 물질

4

반응물 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86664673tert-Butyl (1-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate

생성물 1

HCID 675034241-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochloride수율 92.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl (1-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (11.3 mg, 0.0189 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 17.5 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (10.6 mg, 92.7%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.73 (s, 1H), 8.67 (br s, 3H), 8.16 (dd, J=4.8, 1.6 Hz, 1H), 8.00 (dd, J=7.9, 1.6 Hz, 1H), 7.75-7.71 (m, 1H), 7.68-7.64 (m, 1H), 7.63-7.49 (m, 4H), 7.46-7.31 (m, 4H), 7.21-7.13 (m, 1H), 6.95 (dd, J=7.9, 1.6 Hz, 1H), 6.77 (dd, J=7.9, 4.8 Hz, 1H), 2.70-2.43 (m, 4H), 2.27-2.13 (m, 1H), 1.93-1.78 (m, 1H); LCMS: 497 [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-1480a6f2ba214976ac248ee7310aaedf
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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