Sodium Carbonate → 1-Methylethyl 4-({[6-(4-{[(2-hydroxyethyl)amino]sulfonyl}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423561

반응식

HRID 423561 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[N:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=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[N:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]3)=[CH:20][CH: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 86638737HCID 86638737, 화합물

생성물 1

HCID 249927531-Methylethyl 4-({[6-(4-{[(2-hydroxyethyl)amino]sulfonyl}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate수율 27%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

The title compound (70 mg, 27%) was prepared as a white solid from (4-{[(2-hydroxyethyl)amino]sulfonyl}phenyl)boronic acid (130 mg, 0.55 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 197 mg, 0.55 mmol), Pd(PPh3)2Cl2 (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 8.36 (d, 1H, J=2.9 Hz), 8.05 (d, 2H, J=8.6 Hz), 7.91 (d, 2H, J=8.6 Hz), 7.69 (d, 1H, J=8.8 Hz), 7.26 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 5.11 (t, 1H, J=6.0 Hz), 4.96-4.83 (m, 1H), 4.20 (bs, 2H), 3.89 (d, 2H, J=6.2 Hz), 3.70-3.61 (m, 2H), 3.13-2.99 (m, 2H), 2.83-2.70 (m, 2H), 2.07-1.92 (m, 1H), 1.89-1.79 (m, 2H), 1.70 (bs, 1H), 1.37-1.17 (m, 8H); LRMS (ESI), m/z 478 (M+H).

출처 및 근거

ORD 기록
ord-a5f4b26ff8dc4aadb7b027755a2bad53
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

연결된 노트

불러오는 중…