Triethylamine → HCID 19028016, compound

HRID 2257128Notes

Reaction equation

HRID 2257128 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[CH:9][C:8]=2[O:16][CH3:17])[N:6]=1.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]([C:28](O)=[O:29])[CH:19]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:17][O:16][C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([O:13][CH3:14])[C:7]=1[C:5]1[N:6]=[C:2]([NH:1][C:28]([C:20]2[CH:19]=[N:18][C:27]3[C:22]([CH:21]=2)=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:29])[S:3][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 80971Quinoline-3-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 15224835HCID 15224835, compound

Product 1

HCID 19028016HCID 19028016, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of 2-amino-4-(2,6-dimethoxy-4-methylphenyl)-thiazole, 0.76 g of 3-quinolinecarboxylic acid, 0.65 ml of triethylamine and 2.15 g of BOP are dissolved in 10 ml of DMF, and the reaction mixture is left at r.t. for 48 hours. It is then poured into pH 2 buffer solution, a precipitate is separated by filtration, and the yellow solid is successively washed with water, stirred in 5% sodium carbonate solution, filtered off and thereafter dissolved in DCM. The solution is washed with 5% sodium carbonate solution and then, successively, the organic phase is separated after settling has taken place, dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is stirred in ether, filtered off and dried to yield 1.58 g of the expected compound, m.p.=245°246° C.

Workup

  1. customa precipitate is separated by filtration
  2. washthe yellow solid is successively washed with water
  3. filtrationfiltered off
  4. dissolutiondissolved in DCM
  5. washThe solution is washed with 5% sodium carbonate solution
  6. customsuccessively, the organic phase is separated after settling
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. stirringThe residue is stirred in ether
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-e1c5b73defa04e199b3d2125a8190f7e
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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