Dimethylbarbituric acid → N-({5-[(4-heptanoylpiperidin-1-yl)sulfonyl]thien-2-yl}methyl)-3-methoxybenzamide

HRID 906645

반응식

HRID 906645 반응식
C([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14]([N:17]2[CH2:22][CH2:21][CH:20]([C:23](=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:11][CH:10]=1)CC=C)C=C.CN1C(=O)CC(=O)N(C)C1=O.CCN(C(C)C)C(C)C.[C:51](Cl)(=[O:60])[C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH3:59])[CH:53]=1>C(Cl)Cl.C1COCC1.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>[C:23]([CH:20]1[CH2:19][CH2:18][N:17]([S:14]([C:12]2[S:13][C:9]([CH2:8][NH:4][C:51](=[O:60])[C:52]3[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH3:59])[CH:53]=3)=[CH:10][CH:11]=2)(=[O:16])=[O:15])[CH2:22][CH2:21]1)(=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

참가 물질

9

반응물 4

HCID 69860Dimethylbarbituric acidHCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 674035001-[1-({5-[(Diallylamino)methyl]thien-2-yl}sulfonyl)piperidin-4-yl]heptan-1-one

생성물 1

HCID 57443912N-({5-[(4-heptanoylpiperidin-1-yl)sulfonyl]thien-2-yl}methyl)-3-methoxybenzamide수율 50%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 327c (100 mg, 0.22 mmol), 1,3-Dimethylbarbituric acid (69 mg, 0.44 mmol) and Tetrakis(triphenylphosphine)palladium (12 mg, 0.01 mmol) were stirred in 3 mL CH2Cl2 overnight. The deprotection was followed by TLC. After complete cleavage of the protecting groups, the solvent was evaporated to dryness. The crude was taken up in THF, DIEA (76 ul, 0.33 mmol) was added, followed by the slow addition of 3-anisoylchloride (38 mg, 0.22 mmol) in THF. The reaction was stirred for 3 h, diluted with EtOAc and extracted with NaHCO3 and brine. The organic layers were dried over Na2SO4 and evaporated to dryness. The crude mixture was purified by flash chromatography on silica gel using cyclohexane/EtOAc 1:1 as eluent to obtain 30 mg (50%) of 327 as a colorless oil: H1 NMR (CDCl3) δ 7.40-7.10 (m, 3H), 6.95 (m, 2H), 6.45 (m, 1H), 4.70 (d, J=6.0 Hz, 2H), 3.74 (s, 3H), 3.58 (m, 2H), 2.40 (m, 2H), 2.27 (t, J=7.5 Hz, 2H), 2.19 (m, 1H), 1.77 (m, 2H), 1.64 (m, 2H), 1.13 (m, 8H), 0.74 (t, J=6.8 Hz, 3H), M/Z APCI: 506.3 (M+1).

후처리

  1. customAfter complete cleavage of the protecting groups, the solvent was evaporated to dryness
  2. extractionextracted with NaHCO3 and brine
  3. dry with materialThe organic layers were dried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude mixture was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-343638b4a410443a8e80af95cd7a89c1
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012995B1

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