Cesium carbonate → HCID 86711412, compound

HRID 926339Notes

Reaction equation

HRID 926339 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12.[NH:19]1[CH:23]=[CH:22][N:21]=[N:20]1.CN(C)[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu]I.O>[N:19]1[N:20]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][N:6]2[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]23)[N:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dioneHCID 178418936HCID 178418936, compound

Product 1

HCID 86711412HCID 86711412, compoundYield 19.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

136-1. A mixture of 9-iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (600 mg, 1.69 mmol), 1H-1,2,3-triazole (421 mg, 6.10 mmol), trans-N,N-dimethylcyclohexane-1,2-diamine (87 mg, 0.61 mmol), cesium carbonate (1987 mg, 6.10 mmol) and CuI (323 mg, 1.69 mmol) in DMF (6 mL) were heated under Ar at 130° C. in the microwave for 5 hr. The mixture was cooled to rt. Water was added and the mixture was extracted with CH2Cl2 (2×). The combined organic layers were dried with sodium sulfate and evaporated under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: DCM for 4 min, then from 0% MeOH in DCM to 5% MeOH in DCM in 26 min, followed by 5% MeOH in DCM for 5 min) to yield the title compound as yellow oil (97 mg). UPLC-MS: MS 296.2 (M+H+); UPLC rt 0.63 min.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionthe mixture was extracted with CH2Cl2 (2×)
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent
  6. waitfrom 0% MeOH in DCM to 5% MeOH in DCM in 26 min
  7. waitfollowed by 5% MeOH in DCM for 5 min

Sources & evidence

ORD record
ord-2f8cece1e2d44919be1918b1192f6c85
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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