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Hydrochloric Acid → 2-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-5-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-one hydrochloride

HRID 474956
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HRID 474956 반응식
[ClH:1].[CH3:2][N:3]1[C:11]2[CH:10]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]4[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[CH:14]=[N:13]3)[CH:8]=[CH:7][C:6]=2[C:5]2[CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][CH2:34][CH2:35][C:4]1=2>CO>[ClH:1].[CH3:2][N:3]1[C:11]2[CH:10]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]4[CH:22]=[N:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=4)[CH:14]=[N:13]3)[CH:8]=[CH:7][C:6]=2[C:5]2[CH2:31][NH:32][CH2:33][CH2:34][CH2:35][C:4]1=2
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 66873698tert-butyl 6-methyl-8-(6-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-1(6H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

생성물 1

HCID 668731582-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-5-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-one hydrochloride수율 61%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1.25 M HCl in MeOH (4.0 mL) was added to tert-butyl 6-methyl-8-(6-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-1(6H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (43 mg, 0.075 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was concentrated under reduced pressure, and the resulting residue was diluted with MeOH (1.0 mL) and Et2O (10 mL). The resulting solids were collected by filtration to provide the title compound (23 mg, 61%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 8.91 (d, J=1.5 Hz, 1H), 8.87 (s, 2H), 8.22 (dd, J=8.5, 1.5 Hz, 1H), 8.02-8.00 (m, 2H), 7.64 (d, J=8.5 Hz, 1H), 7.57 (d, J=1.5 Hz, 1H), 7.13 (dd, J=8.5, 2.0 Hz, 1H), 6.56 (d, J=3.0 Hz, 1H), 5.41 (s, 2H), 4.44 (s, 2H), 3.72 (s, 3H), 3.47-3.43 (m, 2H), 3.10 (t, J=5.5 Hz, 2H), 2.08-2.04 (m, 2H); ESI MS m/z 470 [M+H]+; HPLC (Method A)>99% (AUC), tR=14.1 min.

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with MeOH (1.0 mL) and Et2O (10 mL)
  3. filtrationThe resulting solids were collected by filtration

출처 및 근거

ORD 기록
ord-b853059c44c5416d9e2680dd78f28cf7
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637501B2

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