N,N'-Dimethylethylenediamine → HCID 59618741, compound

HRID 1691472Notes

Reaction equation

HRID 1691472 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22](I)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=[CH:29][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:34]1[CH:38]=[CH:37][N:36]=[N:35]1.CNCCNC.CC([O-])(C)C.[K+]>CN(C=O)C.CCOC(C)=O.[Cu]I>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([N:35]4[N:36]=[CH:37][CH:38]=[N:34]4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=[CH:29][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 23665647Potassium tert-butoxideHCID 66901702HCID 66901702, compound2×HCID 178418936HCID 178418936, compound

Product 1

HCID 59618741HCID 59618741, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a stirred solution of 6-[(4-tert-butylphenyl)sulfonyl]-8-iodo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 52, 109 mg, 0.19 mmol) in DMF (4 mL) was added 1,2,3-triazole (39 mg, 0.56 mmol), CuI (71 mg, 0.37 mmol), N,N′-dimethylethylenediamine (0.08 mL, 0.74 mmol), and KOtBu (1.0M/THF, 1.5 mL, 1.5 mmol). The resulting solution was heated to 180° C. in a microwave reactor for 1 h. The solution was diluted with EtOAc and washed with sat aqueous NaHCO3. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated, and the oily residue was purified by silica gel chromatography to give the title compound. 1H NMR (500 MHz, (CD3)2CO): δ 8.60 (s, 1H), 8.20 (s, 1H), 8.00 (m, 2H), 7.78 (d, 1H), 7.50 (d, 1H), 7.22 (d, 2H), 7.18 (d, 1H), 7.05 (d, 2H), 4.90 (br s, 2H), 1.20 (s, 9H). LCMS: m/e 529.0 (M+H)+.

Workup

  1. washwashed
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe oily residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ec3e2ae2f6b40fea61a3ad05931a377
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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