Cesium carbonate → 2-({3-[1-(cyclohexylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide

HRID 601289노트

반응식

HRID 601289 반응식
[CH:1]1([NH:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([OH:18])=[C:10]([C:19]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:22]=4[S:21](=[O:31])(=[O:30])[N:20]=3)[C:9]2=[O:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:40][C:41]([NH2:43])=[O:42]>CN(C)C=O>[CH:1]1([NH:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([OH:18])=[C:10]([C:19]3[NH:24][C:23]4[CH:25]=[CH:26][C:27]([O:29][CH2:40][C:41]([NH2:43])=[O:42])=[CH:28][C:22]=4[S:21](=[O:30])(=[O:31])[N:20]=3)[C:9]2=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 1363742711-(cyclohexylamino)-4-hydroxy-3-(7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)quinolin-2(1H)-one

생성물 1

HCID 1363737832-({3-[1-(cyclohexylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The product of Example 306C (13 mg, 0.028 mmol) in N,N-dimethylformamide (5 mL) was reacted with cesium carbonate (0.0137 g, 0.114 mol) and 2-bromoacetamide (0.008 g, 0.058 mmol) according to the procedure as described in Example 304J to give the title compound. The sodium salt was prepared according to the procedure of Example 1D (7 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.36 (m, 10 H) 2.96 (bs, 1 H) 4.49 (s, 2 H) 5.67 (d, J=4.04 Hz, 1 H) 7.04 (t, J=7.54 Hz, 1 H) 7.20 (m, 3 H) 7.40 (s, 1 H) 7.47 (m, 1 H) 7.62 (s, 1 H) 7.74 (d, J=8.46 Hz, 1 H) 8.05 (d, J=6.62 Hz, 1 H) 16.26 (s, 1 H). (ESI−) m/z 510 (M−H)−, m/z 532 (M+Na−H)−1.

출처 및 근거

ORD 기록
ord-e176511cb65e48b290d9a84f2de00f50
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902203B2

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