Water → HCID 68784936、化合物

HRID 2093590ノート

反応式

HRID 2093590 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[C:7](B(O)O)([CH3:9])=[CH2:8].Cl[C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26][NH:27][C:28](=[O:49])[C:29]3[CH:34]=[CH:33][C:32]([C:35]4[O:36][C:37]5[C:43]([CH:44]([CH3:46])[CH3:45])=[CH:42][C:41]([C:47]#[N:48])=[CH:40][C:38]=5[N:39]=4)=[CH:31][CH:30]=3)[CH2:22][CH2:21]2)[CH:17]=[CH:16][N:15]=1.O>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(O)C>[C:47]([C:41]1[CH:42]=[C:43]([CH:44]([CH3:46])[CH3:45])[C:37]2[O:36][C:35]([C:32]3[CH:33]=[CH:34][C:29]([C:28]([NH:27][CH2:26][CH:23]4[CH2:24][CH2:25][N:20]([C:18]5[CH:17]=[CH:16][N:15]=[C:14]([C:7]([CH3:9])=[CH2:8])[N:19]=5)[CH2:21][CH2:22]4)=[O:49])=[CH:30][CH:31]=3)=[N:39][C:38]=2[CH:40]=1)#[N:48]

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 25169790N-{[1-(2-Chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide

生成物 1

HCID 68784936HCID 68784936、化合物収率 61%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

Sodium carbonate (120 uL, 2M aqueous), isopropenylboronic acid (21 mg), and N-{[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]methyl}-4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzamide (31 mg, EXAMPLE 7) were dissolved in toluene (2.1 ml), water (0.6 ml) and ethanol (0.3 ml). To this solution was added palladium tetrakis(triphenylphosphine) (10 mg). The mixture was heated to 150° C. for 25 min in a microwave reactor. Upon cooling, the mixture was then concentrated in vacuo, taken up in dichloromethane, and purified via flash chromatography on a Biotage Horizon, 25 M column, eluting with 10 column volumes of ethyl acetate to provide the title compound (19 mg, 61%). Mass spectrum (ESI) 521.4 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.5 Hz, 2H), 8.23 (d, J=6.2 Hz, 1H), 7.95 (d, J=8.0 Hz, 3H), 7.52 (s, 1H), 6.38 (d, J=6.2 Hz, 1H), 6.31 (t, J=6.0 Hz, 1H), 6.30 (s, 1H), 5.41 (s, 1H), 4.52 (d, J=8.7 Hz, 2H), 3.46 (m, 3H), 2.91 (t, J=12.4 Hz, 2H), 2.19 (s, 3H), 2.00 (m, 2H), 1.90 (d, J=12.2 Hz, 2H), 1.46 (d, J=7.0, 6H), 1.33 (m, 2H).

後処理

  1. temperatureUpon cooling
  2. concentrationthe mixture was then concentrated in vacuo
  3. custompurified via flash chromatography on a Biotage Horizon, 25 M column
  4. washeluting with 10 column volumes of ethyl acetate

出典と根拠

ORDレコード
ord-3ae416a5af224897a7014aee075d59bd
出典データセット
uspto-grants-2013_05
特許番号
US08445480B2

反応ノート

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