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Diisopropylethylamine → 4-(((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexyl)amino)-2-((2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethyl)amino)pyrimidine-5-carbonitrile

HRID 1749511
ノート
印刷プレビュー

反応式

HRID 1749511 の反応式
[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=2)[CH2:4][C:3]1([CH3:22])[CH3:21].[NH2:23][CH2:24][CH2:25][N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28](C)[C:27]1=[O:36].CCN(C(C)C)C(C)C>C1COCC1>[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([NH:23][CH2:24][CH2:25][N:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[NH:28][C:27]3=[O:36])[N:10]=2)[CH2:4][C:3]1([CH3:22])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 289166861-(2-Amino-ethyl)-3-methyl-1,3-dihydro-benzoimidazol-2-oneHCID 1181621034-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile

生成物 1

HCID 1181794234-(((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexyl)amino)-2-((2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)ethyl)amino)pyrimidine-5-carbonitrile収率 27.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile (100 mg, 0.308 mmol), 1-(2-amino-ethyl)-3-methyl-1,3-dihydro-benzoimidazol-2-one (140 mg, crude), and DIEA (85 mg, 0.66 mmol) in THF (3 mL) was stirred at 100° C. in a microwave reactor for 1.5 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by preparative standard methods to afford the title compound (36.7 mg, 0.084 mmol, 24% yield over 2 steps). 1H NMR (400 MHz, CD3OD) δ (ppm) 8.08-7.94 (m, 1H), 7.11-7.08 (m, 4H), 4.26-4.10 (m, 3H), 3.89-3.66 (m, 2H), 3.40-3.35 (m, 4H), 1.96-1.51 (m, 6H), 1.05-0.99 (m, 6H). MS (ESI) m/z 436.2 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by preparative standard methods

出典と根拠

ORDレコード
ord-efbf391893d24502a7311d48d79c21a5
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09156798B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート