Morpholine → HCID 58765296, compound

HRID 1394882Notes

Reaction equation

HRID 1394882 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7]1([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:32]([O:34][CH3:35])=[O:33])=[CH:18][C:19]=3[N:20]3[CH2:26][C:25](=O)[CH2:24][C:23]4[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=4[C:21]=23)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH:7]1([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([C:32]([O:34][CH3:35])=[O:33])=[CH:18][C:19]=3[N:20]3[CH2:26][CH:25]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH2:24][C:23]4[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=4[C:21]=23)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 58765241methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 58765296HCID 58765296, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

Zinc chloride (21 mg, 0.15 mmol) and morpholine (40 μL, 0.46 mmol) were added to methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (30 mg, 0.078 mmol) in MeOH (3 mL). The mixture was heated at 60° C. for 3 hr when sodium cyanoborohydride (29 mg, 0.46 mmol) was added. Heating was continued for another hr. The mixture was concentrated and the crude product purified by chromatography on a SiO2 preparative plate using dichloromethane containing 2 N methanolic ammonia (100:1). to afford the product as a light yellow solid (25 mg, 70%). ESI-MS m/z 806 (MH+); 1H NMR (500 MHz, MeOD) δ 1.28-1.36 (m, 1 H) 1.36-1.53 (m, 2 H) 1.59-1.71 (m, 1 H) 1.74-1.86 (m, 2H) 1.92-2.19 (m, 4 H) 2.36-2.53 (m, 1 H) 2.58 (m, 1 H) 2.73 (m, 2 H) 2.89 (m, 1 H) 2.99 (m, 1 H) 3.12 (m, 1 H) 3.38 (m, 1 H) 3.58-3.77 (m, 4 H) 3.86-4.00 (m, 3 H) 4.04-4.17 (m, 1 H) 4.51-4.66 (m, 1 H) 7.35-7.50 (m, 4 H) 7.71 (d, J=8.55 Hz, 1 H) 7.88 (m, 1 H) 8.13 (m, 1 H).

Workup

  1. additionwas added
  2. temperatureHeating
  3. waitwas continued for another hr
  4. concentrationThe mixture was concentrated
  5. customthe crude product purified by chromatography on a SiO2 preparative plate

Sources & evidence

ORD record
ord-9dd81d06de574655ad0187664802411d
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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