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

HRID 906645
ノート
印刷プレビュー

反応式

HRID 906645 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-343638b4a410443a8e80af95cd7a89c1
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012995B1

反応ノート

読み込み中…

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