Water → HCID 68784936, 화합물

HRID 2093590노트

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HRID 2093590 반응식
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]

참가 물질

8

반응물 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

생성물 1

HCID 68784936HCID 68784936, 화합물수율 61%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 1140Toluene용매

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온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3ae416a5af224897a7014aee075d59bd
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445480B2

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