1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950662、化合物

HRID 83006

反応式

HRID 83006 の反応式
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][O:8][CH:9]1[CH2:12][NH:11][CH2:10]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:34]([N:37]([CH:40]([CH3:42])C)[CH2:38][CH3:39])(C)C.Cl.[O:44]=[C:45]1[NH:54][C:53]2[N:52]=[CH:51][C:50](/[CH:55]=[CH:56]/[C:57](O)=[O:58])=[CH:49][C:48]=2[CH2:47][CH2:46]1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:34][N:37]1[CH2:38][CH2:39][C:46]2([CH2:47][C:48]3[C:53](=[N:52][CH:51]=[C:50](/[CH:55]=[CH:56]/[C:57](=[O:58])[N:11]4[CH2:12][CH:9]([O:8][CH2:7][C:3]5[S:2][CH:6]=[CH:5][CH:4]=5)[CH2:10]4)[CH:49]=3)[NH:54][C:45]2=[O:44])[CH2:42][CH2:40]1

参加物

9

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 671545443-(2-Thienylmethoxy)azetidine hydrochloride

生成物 1

HCID 52950662HCID 52950662、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-(Thiophen-2-ylmethoxy)-azetidine hydrochloride (45.8 mg, 0.22 mmol), EDCI (40.26 mg, 0.21 mmol), HOBt (28.5 mg, 0.21 mmol) and diisopropylethylamine (62 μL, 0.35 mmol) were successively added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride (47.0 mg, 0.14 mmol) in dimethylformamide (5 mL) at room temperature. The reaction mixture was stirred overnight and then diluted by addition of ethyl acetate (20 ml) and water (20 mL). The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×20 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (95:5 to 0:1) as eluent. After precipitation in a mixture dichloromethane/diethylether/pentane, the title product was obtained as a white solid (12 mg, 24%).

後処理

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel
  8. customAfter precipitation in a mixture dichloromethane/diethylether/pentane

出典と根拠

ORDレコード
ord-f017931b584746f99e7452558eaa47da
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

関連ノート

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