Hydrochloric Acid → HCID 10253417, 화합물

HRID 346789

반응식

HRID 346789 반응식
[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

참가 물질

8

반응물 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

생성물 2

HCID 10253417HCID 10253417, 화합물HCID 21082149N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)butyramide

시약·촉매·용매 2

HCID 887Methanol용매HCID 225585302-Butanone ethanol용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-a546b773c4bb4beebee5ed137649b1a7
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173045B2

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