Dimethylformamide → HCID 59814744, compound

HRID 1994452Notes

Reaction equation

HRID 1994452 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([N:9]1[C:22]3[CH:21]=[CH:20][C:19](Br)=[CH:18][C:17]=3[S:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:2]2.[CH3:24][N:25](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([N:9]1[C:22]3[CH:21]=[CH:20][C:19]([C:24]#[N:25])=[CH:18][C:17]=3[S:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:2]2

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 59814692HCID 59814692, compound2×

Product 1

HCID 59814744HCID 59814744, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
160 °C

Procedure

To a solution of 10-(8-aza-bicyclo[3.2.1]oct-3-yl)-3-bromo-10H-phenothiazine, 4i (50 mg, 0.13 mmol) in DMF (750 μL) was added zinc cyanide (15 mg, 0.13 mmol) and tetrakistriphenylphosphine palladium (4 mg), the solution was purged with nitrogen, and the mixture was heated in the microwave for 5 min at 160° C. The mixture was allowed to cool to rt, and purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield title compound 10-(8-aza-bicyclo[3.2.1]oct-3-yl)-10H-phenothiazine-3-carbonitrile, 1aa as a TFA salt and as a mixture of endo and exo isomers. MS m/z (MH+) 334.1.

Workup

  1. customthe solution was purged with nitrogen
  2. temperatureto cool to rt
  3. custompurified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-c9ec9e1bbb3c4e4c8936d4c18c74d6af
Source dataset
uspto-grants-2010_01
Patent number
US07652005B2

Reaction notes

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