1H-Imidazole-1-propanamine → HCID 178461588, compound

HRID 1941773Notes

Reaction equation

HRID 1941773 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[O:14][CH2:15][C@H:16]([CH3:17])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:23])[C:5]([C:18]1[NH:22][N:21]=[N:20][N:19]=1)=[CH:6]3.[N:24]1([CH2:29][CH2:30][CH2:31][NH2:32])[CH:28]=[CH:27][N:26]=[CH:25]1>CS(C)=O>[N:24]1([CH2:29][CH2:30][CH2:31][NH:32][C:10]2[C:9]3[O:14][CH2:15][C@H:16]([CH3:17])[N:7]4[C:8]=3[C:3]([C:4](=[O:23])[C:5]([C:18]3[NH:22][N:21]=[N:20][N:19]=3)=[CH:6]4)=[C:2]([NH2:1])[C:11]=2[F:12])[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

4

Reactant 2

HCID 787361H-Imidazole-1-propanamineHCID 178461587HCID 178461587, compound

Product 1

HCID 178461588HCID 178461588, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of 13 (250 mg, 0.78 mmol) in 5 ml of DMSO were added 132 μl (1.17 mmol) of 3-(1H-imidazol-1-yl)propan-1-amine. The reaction mixture was heated to 120° C. for 1 h. Upon completion of the reaction the DMSO was removed and the remaining solid was purified by preparative HPLC. To the combined HPLC fractions containing the product were added several drops of 1 N HCl before they were dried down to generate the HCl salt of the compound. The title compound was obtained as a yellow solid (118 mg, 37% yield).

Workup

  1. customwas removed
  2. customthe remaining solid was purified by preparative HPLC
  3. additionTo the combined HPLC fractions containing the product
  4. additionwere added several drops of 1 N HCl before they
  5. customwere dried down

Sources & evidence

ORD record
ord-a640d2ff97464b81b87ac0f9c4b9fb60
Source dataset
uspto-grants-2013_03
Patent number
US08389514B2

Reaction notes

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