Sodium Carbonate Monohydrate → HCID 178476517, 화합물

HRID 432325노트

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HRID 432325 반응식
[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13](B3[O:20][C:19]([CH3:22])(C)C(C)(C)O3)=[CH:12][CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:26]1[C:34]2[C:29](=[N:30][CH:31]=[N:32][C:33]=2[NH2:35])[N:28]([C@H:36]2[CH2:41][CH2:40][C@@H:39]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)[CH2:38][CH2:37]2)[N:27]=1.O.[C:50](=[O:53])([O-])[O-:51].[Na+].[Na+]>COCCOC.O>[C:19]([OH:51])(=[O:20])[CH3:22].[C:50]([OH:51])(=[O:53])[CH3:1].[CH3:48][N:45]1[CH2:46][CH2:47][N:42]([C@@H:39]2[CH2:38][CH2:37][C@H:36]([N:28]3[C:29]4=[N:30][CH:31]=[N:32][C:33]([NH2:35])=[C:34]4[C:26]([C:13]4[CH:12]=[CH:11][C:10]([NH:9][CH:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH3:8])=[CH:15][CH:14]=4)=[N:27]3)[CH2:41][CH2:40]2)[CH2:43][CH2:44]1

참가 물질

6

반응물 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22346898α-Methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenemethanamineHCID 178481014HCID 178481014, 화합물

생성물 1

HCID 178476517HCID 178476517, 화합물수율 83.7%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of N-(1-phenylethyl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.070 g, 0.000235 mol), cis-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.080 g, 0.000181 mol), tetrakis-(triphenylphosphine)palladium (0.012 g, 0.000011 mol) and sodium carbonate monohydrate (0.056 g, 0.00045 mol) was heated in a mixture of ethylene glycol dimethyl ether (5 mL) and water (3 mL) at 80° C. for sixteen hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield Cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-{4-[(1-phenylethyl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.062 g, 0.0000984 mol) as a white solid.

후처리

  1. customsolvents were removed under the reduced pressure
  2. customThe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

출처 및 근거

ORD 기록
ord-bfc4f65525b6409299dead8e4eb0fbce
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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