Diisopropylethylamine → 4-{5-Imidazolyl-2-[(2-{[5-(trifluoromethyl) (2-pyridyl)]amino}ethyl)amino]pyrimidin-4-yl}benzenecarbonitrile

HRID 1823434

反応式

HRID 1823434 の反応式
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[C:8]([C:19]2[NH:20][CH:21]=[CH:22][N:23]=2)=[CH:7][N:6]=1.Cl[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[NH:20]1[CH:21]=[CH:22][N:23]=[C:19]1[C:8]1[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[N:10][C:5]([NH:4][CH2:3][CH2:2][NH:1][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 57231913HCID 57231913、化合物

生成物 1

HCID 571424814-{5-Imidazolyl-2-[(2-{[5-(trifluoromethyl) (2-pyridyl)]amino}ethyl)amino]pyrimidin-4-yl}benzenecarbonitrile収率 5%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-{2-[(2-aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile (30 mg, 0.098 mmol), 2-chloro-5-(trifluoromethyl)pyridine (18 mg, 0.098 mmol), and Hünig's base (70 uL, 0.4 mmol) in DMA (500 uL) were heated to 80° C. After stirring for 12 hours, the reaction was diluted with ethyl acetate (10 ml) and extracted with sat. aq. NaHCO3 (2×5 ml), water (3×5 ml), brine (5 ml), dried with Na2SO4, filtered, and concentrated. The product was purified by preparative HPLC using a reverse phase column and a water/acetonitrile gradient. The product 4-{5-imidazolyl-2-[(2-{[5-(trifluoromethyl)(2-pyridyl)]amino}ethyl)amino]pyrimidin-4-yl}benzenecarbonitrile was obtained as a off-white solid in 5% yield.

後処理

  1. extractionextracted with sat. aq. NaHCO3 (2×5 ml), water (3×5 ml), brine (5 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-5f6b416d87b04a0a93fc8141941371ce
出典データセット
uspto-grants-2006_05
特許番号
US07037918B2

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