Sodium Carbonate Monohydrate → HCID 178480957、化合物

HRID 897476ノート

反応式

HRID 897476 の反応式
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH:17]=2)[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:32]1[C:40]2[C:35](=[N:36][CH:37]=[N:38][C:39]=2[NH2:41])[N:34]([C@H:42]2[CH2:47][CH2:46][C@@H:45]([N:48]3[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]3)[CH2:44][CH2:43]2)[N:33]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[NH2:41][C:39]1[N:38]=[CH:37][N:36]=[C:35]2[N:34]([C@H:42]3[CH2:47][CH2:46][C@@H:45]([N:48]4[CH2:49][CH2:50][N:51]([CH3:54])[CH2:52][CH2:53]4)[CH2:44][CH2:43]3)[N:33]=[C:32]([C:19]3[CH:18]=[CH:17][C:16]([CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:21][CH:20]=3)[C:40]=12

参加物

6

反応物 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22347089Tert-butyl n-{phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamateHCID 178481014HCID 178481014、化合物

生成物 1

HCID 178480957HCID 178480957、化合物収率 69.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of tert-butyl N-{phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamate (3.0 g, 0.00733 mol), cis-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.4 g, 0.0054 mol), tetrakis-(triphenylphosphine)palladium (0.381 g, 0.00033 mol) and sodium carbonate monohydrate (1.69 g, 0.0136 mol) was heated in a mixture of ethylene glycol dimethyl ether (80 mL) and water (40 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 partitioned between saturated aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL), the organic layer separated and the aqueous layer further extracted with ethyl acetate twice (100 mL each). The combined organic extracts were dried over magnesium sulfate. The solvents were evaporated under reduced pressure to leave a tan solid which was purified by flash column chromatography on silica using dichloromethane/triethylamine/methanol (96:3:1) as a mobile phase to give cis-tert-butyl N-[(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)(phenyl)-methyl]carbamate (2.24 g, 0.00375 mol) as a white solid.

後処理

  1. customsolvents were removed under the reduced pressure
  2. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL)
  3. customthe organic layer separated
  4. extractionthe aqueous layer further extracted with ethyl acetate twice (100 mL each)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customThe solvents were evaporated under reduced pressure
  7. customto leave a tan solid which
  8. customwas purified by flash column chromatography on silica

出典と根拠

ORDレコード
ord-7945f85ac2b64d54872bac1798a93e2b
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

反応ノート

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