Hydrochloric Acid → 4-(4-Chlorobenzyloxy)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)pyridin-2(1H)-one dihydrochloride

HRID 1020532노트

반응식

HRID 1020532 반응식
C(OC([N:8]1[CH2:37][CH2:36][C:11]2[N:12]([CH3:35])[C:13]3[CH:14]=[C:15]([N:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=5)=[CH:21][C:20]4=[O:34])[CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:38]>CO.CCOCC>[ClH:33].[ClH:38].[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][O:25][C:22]2[CH:23]=[CH:24][N:19]([C:15]3[CH:16]=[CH:17][C:18]4[C:10]5[CH2:9][NH:8][CH2:37][CH2:36][C:11]=5[N:12]([CH3:35])[C:13]=4[CH:14]=3)[C:20](=[O:34])[CH:21]=2)=[CH:32][CH:31]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 57950458tert-Butyl 7-(4-(4-chlorobenzyloxy)-2-oxopyridin-1(2H)-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

생성물 1

HCID 686579064-(4-Chlorobenzyloxy)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)pyridin-2(1H)-one dihydrochloride수율 71%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

tert-Butyl-7-(4-(4-chlorobenzyloxy)-2-oxopyridin-1(2H)-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (143 mg, 0.275 mmol) was dissolved in MeOH (1 mL) and 2 N HCl in Et2O (5 mL) was added. The reaction was allowed to proceed for 3 h. The resulting precipitate was collected by filtration and washed with Et2O to provide the title compound (95 mg, 71%) as a yellow solid: mp 305-310° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.54 (br s, 2H), 7.57 (m, 2H), 7.51 (s, 5H), 6.99 (d, J=7.8 Hz, 1H), 6.12 (dd, J=7.8, 2.7 Hz, 1H), 5.99 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.33 (br s, 2H), 3.68 (s, 3H), 3.52-3.48 (m, 2H), 3.12-3.08 (m, 2H); ESI MS m/z 420 [M+H]+; HPLC (Method B) 97% (AUC), tR=13.99 min.

후처리

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with Et2O

출처 및 근거

ORD 기록
ord-e0e7c18bbb524442a772fc4a0f08d9e9
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716308B2

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