Sodium Carbonate → N-(2-Hydroxyethyl)-4-{5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-pyridinyl}benzenesulfonamide

HRID 423553

반응식

HRID 423553 반응식
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1)(=[O:7])=[O:6].Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]3[O:36][N:35]=[C:34]([CH:37]([CH3:39])[CH3:38])[N:33]=3)[CH2:28][CH2:27]2)=[CH:20][N:19]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]3[CH2:31][CH2:30][N:29]([C:32]4[O:36][N:35]=[C:34]([CH:37]([CH3:39])[CH3:38])[N:33]=4)[CH2:28][CH2:27]3)=[CH:20][N:19]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 44119332(4-(N-(2-Hydroxyethyl)sulfamoyl)phenyl)boronic acidHCID 866387382-Bromo-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyridine

생성물 1

HCID 24996877N-(2-Hydroxyethyl)-4-{5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-pyridinyl}benzenesulfonamide수율 15%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

The title compound (30 mg, 15%) was prepared as an off-white solid from (4-{[(2-hydroxyethyl)amino]sulfonyl}phenyl)boronic acid (98 mg, 0.4 mmol), 2-bromo-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyridine (153 mg, 0.4 mmol), Pd(PPh3)4 (100 mg, 0.14 mmol), 2M Na2CO3 (2 mL) and DME (4 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.39 (s, 1H), 8.07 (d, 2H, J=8.2 Hz), 7.93 (d, 2H, J=8.2 Hz), 7.72 (d, 1H, J=8.6 Hz), 7.30 (d, 1H, J=6.5 Hz), 5.07 (t, 1H, J=5.8 Hz), 4.28-4.18 (m, 2H), 3.94 (d, 2H, J=6.0 Hz), 3.73-3.65 (m, 2H), 3.17-3.04 (m, 4H), 2.96-2.80 (m, 1H), 2.06-1.92 (m, 3H), 1.57-1.40 (m, 2H), 1.28 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 502 (M+H).

출처 및 근거

ORD 기록
ord-2371ab5bc4bf4fb08045f3dfad338680
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

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