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Dimethylformamide → 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(isoxazol-5-ylmethyl)sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 856534
ノート
印刷プレビュー

反応式

HRID 856534 の反応式
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29](O)=[O:30])=[CH:20][C:19]=3[CH:32]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].CN(C=O)C.S(Cl)(Cl)=O.[O:42]1[C:46]([CH2:47][S:48][C:49]2[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=2)=[CH:45][CH:44]=[N:43]1>O1CCCC1.O.C(N(CC)CC)C>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:22][C:21]([C:29]([NH:53][C:52]4[CH:54]=[CH:55][C:49]([S:48][CH2:47][C:46]5[O:42][N:43]=[CH:44][CH:45]=5)=[CH:50][CH:51]=4)=[O:30])=[CH:20][C:19]=3[CH:32]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 223289057-[4-(2-Butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 432994194-[(Isoxazol-5-ylmethyl)sulfanyl]aniline

生成物 1

HCID 695213457-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(isoxazol-5-ylmethyl)sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide収率 55.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (700 mg) in tetrahydrofuran (15 ml) was added one droplet of DMF. Then, thionyl chloride (0.15 ml) was added to the mixture at 0° C., and the mixture was allowed to be at room temperature and stirred for 1 hour under nitrogen atmosphere. This solution was added to a solution of 4-[(isoxazol-5-ylmethyl)sulfanyl]aniline (429 mg) and triethylamine (5.8 ml) in tetrahydrofuran (15 ml) at 0° C. The mixture was stirred for 1.5 hours at room temperature under nitrogen atmosphere, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) and was recrystallized from hexane-ethyl acetate, to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(isoxazol-5-ylmethyl)sulfanyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (557 mg) (Compound 327) as yellow crystals.

後処理

  1. customto be at room temperature
  2. stirringThe mixture was stirred for 1.5 hours at room temperature under nitrogen atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)
  8. customwas recrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-b09118e128244b0abe3e68a67bd49236
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07262185B2

反応ノート

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