Diisopropylethylamine → (4-{[2-(2-Methanesulfonyl-benzylamino)-5-nitro-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester

HRID 1819492ノート

反応式

HRID 1819492 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18](Cl)[N:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:28][S:29]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35])(=[O:31])=[O:30].C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:35][CH2:34][C:33]3[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=3[S:29]([CH3:28])(=[O:31])=[O:30])[N:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 162183342-(Methanesulfonyl)benzylamine hydrochlorideHCID 57885529(4-[(2-Chloro-5-nitro-pyrimidin-4-ylamino)-methyl]cyclohexyl)-carbamic acid tert-butyl ester

生成物 1

HCID 59845694(4-{[2-(2-Methanesulfonyl-benzylamino)-5-nitro-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester収率 69.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

{4-[(2-Chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (100 mg, 0.26 mmol) was dissolved in DMF (3 mL). 2-Methanesulfonyl-benzylamine hydrochloride (115 mg, 0.52 mmol) and diisopropylethylamine (0.14 mL, 0.78 mmol) were added sequentially. After 24 h, the reaction was partitioned between water (10 mL) and DCM (10 mL). The organic layer was washed with 5% AcOH (aq), saturated Na2CO3 and water, dried over MgSO4, filtered and concentrated. Chromatography (silica, 0-15% MeOH in DCM; Rf=0.3 10% MeOH in DCM) yielded 96 mg of (4-{[2-(2-methanesulfonyl-benzylamino)-5-nitro-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester as a pale yellow solid, m/z 535.7 [M+1]+.

後処理

  1. customthe reaction was partitioned between water (10 mL) and DCM (10 mL)
  2. washThe organic layer was washed with 5% AcOH (aq), saturated Na2CO3 and water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-4eb79b810d664a44967aee8457845d37
出典データセット
uspto-grants-2009_10
特許番号
US07601714B2

反応ノート

読み込み中…