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Hydrochloric Acid → N-{4-[7-chloro-1-(2-hydroxyethyl)-3-oxo-1,3-dihydrocyclobuta[c]quinolin-4(2H)-yl]butyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

HRID 624263
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반응식

HRID 624263 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([N:19]3[CH2:27][C:26]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[CH2:20]3)=[O:18])[C:7](=[O:28])[CH:6]3[CH2:29][CH:30]4[CH2:31][CH2:32][O:33][C:5]34[C:4]=2[CH:3]=1.[OH-].[Na+].Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([N:19]3[CH2:27][C:26]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[CH2:20]3)=[O:18])[C:7](=[O:28])[C:6]3[CH2:29][CH:30]([CH2:31][CH2:32][OH:33])[C:5]=3[C:4]=2[CH:3]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68751788N-[4-(9-chloro-5-oxo-2,3,3a,4,4a,5-hexahydro-6H-furo[2',3':2,3]cyclobuta[1,2-c]quinolin-6-yl)butyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

생성물 1

HCID 57510867N-{4-[7-chloro-1-(2-hydroxyethyl)-3-oxo-1,3-dihydrocyclobuta[c]quinolin-4(2H)-yl]butyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-[4-(9-chloro-5-oxo-2,3,3a,4,4a,5-hexahydro-6H-furo[2′,3′:2,3]cyclobuta[1,2-c]quinolin-6-yl)butyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide (30 mg, 0.064 mmol) in dimethylformamide (292 uL) and water (292 uL) was added sodium hydroxide (1.679 μl, 0.064 mmol). The solution was stirred for 18 hours and then brought to pH ˜7 by dropwise addition of 1M HCl. Column chromatography of the wet, crude mixture provided the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 8.58 (s, 1H), 8.54 (d, J=5.1 Hz, 1H), 7.54 (d, J=2.4 Hz, 1H), 7.46 (dd, J=9.1, 2.4 Hz, 1H), 7.37 (d, J=9.1 Hz, 1H), 7.25 (m, 1H), 5.06 (t, J=5.7 Hz, 1H) 4.77 (bs, 2H), 4.75 (bs, 2H), 4.33 (t, J=7.4 Hz, 2H), 3.87 (m, 2H), 3.74 (m, 2H), 3.46 (m, 2H), 3.37 (dd, J=14.0, 4.5 Hz, 1H), 2.86 (dd, J=14.0, 1.3 Hz, 1H), 2.27 (m, 1H), 1.97 (m, 1H), 1.82 (m, 2H), 1.71 (m, 2H); MS (ESI(+)) m/e 467 (M+H)+.

출처 및 근거

ORD 기록
ord-d2dfc7820db24b36b65edbed61a8763a
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09302989B2

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