3-Pyridinemethanamine → HCID 57500665, compound

HRID 1919675Notes

Reaction equation

HRID 1919675 reaction equation
Cl[C:2]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O-:17])=[O:16])=[CH:5][C:4]=2[N:3]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>CN1C(=O)CCC1.CO>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][NH:18][C:2]2[C:11]3[CH:12]=[CH:13][S:14][C:10]=3[C:9]3[CH:8]=[CH:7][C:6]([C:15]([OH:17])=[O:16])=[CH:5][C:4]=3[N:3]=2)[CH:21]=1

Participants

5

Reactant 2

HCID 310183-PyridinemethanamineHCID 57500663HCID 57500663, compound

Product 1

HCID 57500665HCID 57500665, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
120 °C

Procedure

4-chlorothieno[3,2-c]quinoline-7-carboxylate (10 mg, 0.036 mmol) was suspended in NMP (0.1 ml) and 3-aminomethylpyridine (0.1 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. The reaction mixture was dissolved in a mixture of NMP and MeOH and the ester intermediate purified by preparative HPLC. After genevac evaporation of the solvents, the resulting solid was dissolved in a 1:1 mixture of THF and MeOH (0.6 ml). 5N aqueous LiOH (0.2 ml) was added and the mixture stirred at room temperature for 17 hrs. Water and aqueous HCl were added and the solution of 4-(pyridin-3-ylmethylamino)thieno[3,2-c]quinoline-7-carboxylic acid was purified by preparative HPLC. Removal of the solvents by genevac evaporation provided compound 4-(pyridin-3-ylmethylamino)thieno[3,2-c]quinoline-7-carboxylic acid as a white solid (10 mg, 62% yield). LCMS (ES): 95% pure, m/z 336 [M+1]+. 1H NMR (CDCl3, 400 MHz) δ 5.23 (s, 2H), 7.71-7.78 (m, 4H), 8.11 (d, J=5.6, 1H), 8.47 (d, J=8.0, 1H), 8.49 (d, J=0.8, 1H), 8.62 (d, J=5.2, 1H), 8.97 (s, 1H) ppm.

Workup

  1. customthe ester intermediate purified by preparative HPLC
  2. customAfter genevac evaporation of the solvents
  3. dissolutionthe resulting solid was dissolved in a 1:1 mixture of THF and MeOH (0.6 ml)
  4. addition5N aqueous LiOH (0.2 ml) was added
  5. additionWater and aqueous HCl were added
  6. customthe solution of 4-(pyridin-3-ylmethylamino)thieno[3,2-c]quinoline-7-carboxylic acid was purified by preparative HPLC
  7. customRemoval of the solvents
  8. customby genevac evaporation

Sources & evidence

ORD record
ord-138beef379bb49eba848cf6bcd4fbb67
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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