1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59755964, compound

HRID 1360321Notes

Reaction equation

HRID 1360321 reaction equation
F[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][N:12]([CH3:18])[CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.N12CCCN=C1CCCCC2>N1C=CC=CC=1>[CH3:11][N:12]([CH3:18])[CH:13]1[CH2:17][CH2:16][N:15]([C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:14]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 960892-Fluoronicotinic acidHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 59755964HCID 59755964, compoundYield 116.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of resin B (1.2 mmol/g, 5.0 g, 8.0 mmol) in pyridine (12 mL) was added dimethyl-pyrrolidin-3-yl-amine (1.37 mL, 12 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 2.2 mL, 14.4 mmol) at room temperature. The mixture was agitated at 100° C. for 12 hours under a nitrogen atmosphere. The resin was washed with DCM then MeOH (3×), and dried under vacuum. Compound C was cleaved off the resin with the addition of 50% trifluoroacetic acid in DCM. The mixture was agitated at room temperature for 30 minutes. The resin was washed with DCM (3×), and the filtrate was concentrated using a rotary evaporator. 1 N HCl aqueous solution (2 mL) was added and then lyophilized to yield compound C as a light pink gum (2.2 g). The compound was taken onto the next step without further purification. 1H-NMR δ (CDCl3): 10.85 (s, 1H), 8.26 (dd, 1H, J=4.8 Hz, J=1.6 Hz), 7.96 (dd, 1H, J=7.2 Hz, J=2.0 Hz), 6.81 (dd, 1H, J=7.6 Hz, J=4.8 Hz), 3.92-3.94 (m, 1H), 3.70-3.80 (m, 2H), 3.52-3.54 (m, 1H), 3.43 (m, 1H), 2.80 (m, 6H), 2.20 (m, 1H), 2.17 (m, 1H). ESMS: 236.0 [M+H]+.

Workup

  1. washThe resin was washed with DCM
  2. dry with materialMeOH (3×), and dried under vacuum
  3. additionwith the addition of 50% trifluoroacetic acid in DCM
  4. stirringThe mixture was agitated at room temperature for 30 minutes
  5. washThe resin was washed with DCM (3×)
  6. concentrationthe filtrate was concentrated
  7. customa rotary evaporator
  8. addition1 N HCl aqueous solution (2 mL) was added

Sources & evidence

ORD record
ord-9686623ef087406da8bb5803b8343ee7
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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