(2-Thienylmethyl)amine → HCID 18345001, compound

HRID 869492Notes

Reaction equation

HRID 869492 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.N1(C(N2C=CN=C2)=O)C=CN=C1.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][NH2:33]>C1COCC1>[OH:1][C:2]1[C:3]([C:12]([NH:33][CH2:32][C:28]2[S:27][CH:31]=[CH:30][CH:29]=2)=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 34005(2-Thienylmethyl)amine2×HCID 682631,1'-CarbonyldiimidazoleHCID 2313638-Hydroxyquinoline-7-carboxylic Acid

Product 1

HCID 18345001HCID 18345001, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 8-hydroxyquinoline-7-carboxylic acid (100 mg, 0.53 mmol) and di(1H-imidazol-1-yl)methanone (86 mg, 0.53 mmol) in THF (8 mL) was heated to 45° C. overnight, under nitrogen. The reaction mixture was allowed to cool to RT and thiophene-2-ylmethanamine (30 mg, 0.26 mmol) was added. The resulting mixture was stirred at RT for 24 h. Additional thiophene-2-ylmethanamine (15 mg, 0.1.3 mmol) was added and the reaction mixture was stirred for 60 h at RT. The reaction mixture was quenched with H2O and THF was evaporated to dryness. Saturated solution of sodium hydrogen carbonate was added to the aqueous phase and extracted twice with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1) affording the title compound (40 mg, 0.14 mmol) as a yellow solid.

Workup

  1. temperatureto cool to RT
  2. stirringthe reaction mixture was stirred for 60 h at RT
  3. customThe reaction mixture was quenched with H2O and THF
  4. customwas evaporated to dryness
  5. additionSaturated solution of sodium hydrogen carbonate was added to the aqueous phase
  6. extractionextracted twice with DCM
  7. dry with materialThe separated organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1)

Sources & evidence

ORD record
ord-433db273115e490d931e0b1a3c9fd480
Source dataset
uspto-grants-2015_03
Patent number
US08969380B2

Reaction notes

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