Potassium Carbonate → HCID 10337091, compound

HRID 222761Notes

Reaction equation

HRID 222761 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1F)[C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:1]1([N:5]2[CH2:6][CH2:7][C:8]3[CH:15]=[CH:14][C:13]([O:16][C:25]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=4[F:17])=[CH:12][C:9]=3[CH2:10][CH2:11]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5872033,4-DifluorobenzonitrileHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Product 1

HCID 10337091HCID 10337091, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol (E3) (100 mg, 0.46 mmol), 3,4-difluorobenzonitrile (70 mg, 0.51 mmol) and potassium carbonate (159 mg, 1.15 mmol) in dimethylsulfoxide (2 ml) was heated at 85° C. for 2 hours. The reaction mixture was cooled and applied to a SCX ion exchange cartridge (Varian bond-elute, 10 g) and washed with methanol and then a mixture of 0.880 ammonia/methanol (1:9). The combined basic fractions were concentrated in vacuo to afford the title compound (E271). MS (ES+) m/e 337 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with methanol
  3. additiona mixture of 0.880 ammonia/methanol (1:9)
  4. concentrationThe combined basic fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-f0304d540bef4028a492eabe97751e31
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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