Sodium Carbonate → HCID 68195034, 화합물

HRID 2169650노트

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HRID 2169650 반응식
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]([N:15]([CH3:23])[CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:14])[CH2:7][C@@H:6]3[CH2:24][O:25][CH2:26][CH2:27][N:5]3[C:4]=2[N:3]=1.[NH:28]1[C:36]2[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[C:31]=2[CH:30]=[CH:29]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:28]1[C:36]2[C:31](=[C:32]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([CH2:12][C:13]([N:15]([CH3:23])[CH2:16][CH:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[O:14])[CH2:7][C@@H:6]5[CH2:24][O:25][CH2:26][CH2:27][N:5]5[C:4]=4[N:3]=3)[CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29]1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 27631731H-Indole-4-boronic acidHCID 86670144HCID 86670144, 화합물

생성물 1

HCID 68195034HCID 68195034, 화합물수율 43.7%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

A mixture of (R)-2-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-N-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide (PREPARATION x79, 70 mg, 0.177 mmol), indole-4-boronic acid (42.7 mg, 0.265 mmol), tetrakis(triphenylphosphine)palladium(0) (20.43 mg, 0.018 mmol), and sodium carbonate (37.5 mg, 0.354 mmol) in 1,4-dioxane (0.7 mL) and water (0.35 mL) was heated to 120° C. for 1 hour in a microwave. After cooling to room temperature, the reaction mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica-NH, gradient 0-10% MeOH/CHCl3) to afford the title compound as an off-white solid (36.8 mg, 43.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.04-1.61 (m, 4 H), 1.78-1.97 (m, 1 H), 2.80-3.09 (m, 4 H), 3.12-3.38 (m, 7 H), 3.58 (t, J=9.98 Hz, 2 H), 3.78-4.16 (m, 5 H), 4.41-4.60 (m, 2 H), 7.11 (t, J=7.71 Hz, 1 H), 7.26-7.64 (m, 4 H), 7.86-7.95 (m, 1 H), 11.11 (br s, 1 H); ESI-MS m/z [M+H]+ calc'd for C26H32N6O3, 477.26; found 477.3.

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica-NH, gradient 0-10% MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-66f80354362f4847963ed477a36d8181
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045496B2

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