Sodium Carbonate Monohydrate → HCID 178476517、化合物

HRID 897613ノート

反応式

HRID 897613 の反応式
[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.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>[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

参加物

7

反応物 3

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

生成物 1

HCID 178476517HCID 178476517、化合物収率 83.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dc770ef7652846c797881667c6812e8b
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

反応ノート

読み込み中…