Hydrochloric Acid → HCID 10253417、化合物

HRID 346789

反応式

HRID 346789 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:2]1.[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][C:21]([N:30]([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.[Cl-:33].[CH3:34][O:35]C1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.Cl>CC(=O)CC.C(O)C.CO>[ClH:33].[CH3:31][N:30]([CH3:32])[C:21]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:23][CH:18]([CH2:17][NH:16][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:19][CH2:20]1.[CH3:31][N:30]([CH3:32])[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:20][CH2:19][CH:18]([CH2:17][NH:16][C:34](=[O:35])[CH:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:11][CH3:12])[CH2:23][CH2:22]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8617Indole-3-Butyric AcidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine

生成物 2

HCID 10253417HCID 10253417、化合物HCID 21082149HCID 21082149、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 225585302-Butanone ethanol溶媒

実験手順

4-(1H-Indol-3-yl)butyric acid (232 mg, 1.0 mmol.), the mixture of the diastereoisomers of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (203 mg, 1.0 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (415 mg, 1.5 mmol.) were dissolved in abs. methanol and stirred for 20 h at RT. For working up, the mixture was concentrated and the residue was taken up in water (15 ml), adjusted to pH 11 with 5M NaOH and extracted with EE (4×20 ml). The organic phase was washed with 1M NaOH (3 ml), dried, filtered and concentrated. The residue was a mixture of the bases of the diastereoisomeric target products, which were separated by flash chromatography on silica gel (45 g) (eluant: 700 ml methanol/EE 3:1). The non-polar diastereoisomer was obtained in a yield of 163 mg (0.39 mmol.) and was dissolved in 2-butanone/ethanol (7 ml/2 ml); isopropanolic 5M HCl (125 μl, 0.62 mmol.) was added and stirring was carried out for 2 h at RT. Concentration and drying in vacuo yielded the hydrochloride of the non-polar diastereoisomer of N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)butyramide in the form of a slightly hygroscopic white solid (177 mg, m.p. 95–100° C.).

後処理

  1. dissolutionwere dissolved in abs
  2. concentrationthe mixture was concentrated
  3. extractionextracted with EE (4×20 ml)
  4. washThe organic phase was washed with 1M NaOH (3 ml)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additiona mixture of the bases of the diastereoisomeric target products, which
  9. customwere separated by flash chromatography on silica gel (45 g) (eluant: 700 ml methanol/EE 3:1)
  10. customThe non-polar diastereoisomer was obtained in a yield of 163 mg (0.39 mmol.)
  11. concentrationConcentration
  12. customdrying in vacuo

出典と根拠

ORDレコード
ord-a546b773c4bb4beebee5ed137649b1a7
出典データセット
uspto-grants-2007_02
特許番号
US07173045B2

関連ノート

読み込み中…