Succinic Acid → 2-{4-[1-Methyl-4-(2-methyl-pyridin-4-yl)-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline

HRID 33872

반응식

HRID 33872 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[CH:16][CH:15]=3)=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:32]B1OBOBO1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].C(O)(=O)CCC(O)=O>O1CCOCC1.C(OCC)(=O)C.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>[CH3:13][N:11]1[CH:12]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:32])[CH:7]=2)[C:9]([C:14]2[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:16][CH:15]=2)=[N:10]1

참가 물질

9

반응물 5

HCID 1110Succinic AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 115536722-[4-[4-(2-Chloro-pyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]-phenoxymethyl}-quinolineHCID 177697481CID 177697481

생성물 1

HCID 116899812-{4-[1-Methyl-4-(2-methyl-pyridin-4-yl)-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline

시약·촉매·용매 3

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

반응 조건

온도
100 °C

실험 절차

To a solution of 2-{4-[4-(2-Chloro-pyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]-phenoxymethyl}-quinoline (100 mg) in dioxane (1.2 ml) was added methyl boroxine (0.066 ml), palladium tetrakis (41 mg) and 2N sodium carbonate solution (0.234 ml). The reaction mixture was heated at 100° C. for 8 h, poured into 1 N NaOH, extracted with chloroform, dried magnesium sulfate, filtered and concentrated. Prep TLC run with 3% methanol/0.5% saturated ammonium hydroxide/80% ethyl acetate in hexanes provided the free base material. The produce was stirred in ethyl acetate and 2 eq. of succinic acid was added to give a white precipitate which was filtered to provide the title compound as a white solid succinate salt (20 mg). 1H NMR (400 MHz, DMSO) δ 8.40 (d, J=8.3 Hz, 2 H), 8.25 (d, J=5.0 Hz, 2 H), 8.07 (s, 1H), 8.00 (t, J=7.9 Hz, 2 H), 7.77 (t, J=6.6 Hz, 1 H), 7.67 (d, J=8.7 Hz, 2H), 7.60 (t, J=6.6 Hz, 1 H), 7.29 (d, J=9.1 Hz, 2H), 7.03 (m, 3 H), 6.92 (m, 1H), 5.35 (s, 2H), 3.85 (s, 3H), 2.37 (s, 4H) 2.31 (s, 3H); MS: (M+H m/z=407.0).

후처리

  1. extractionextracted with chloroform, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customprovided the free base material
  5. customto give a white precipitate which
  6. filtrationwas filtered

출처 및 근거

ORD 기록
ord-c1c940f6d47e45c1ac15cf7ce718ecf8
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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