Dimethylformamide → 5-(4-Acetamidobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512527
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:25][C:26]1[S:30][C:29]([NH:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)=[N:28][C:27]=1[C:42]([NH2:44])=[O:43]>C1COCC1.N1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:25][C:26]2[S:30][C:29]([NH:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=3)=[N:28][C:27]=2[C:42]([NH2:44])=[O:43])=[O:11])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 19266p-Acetamidobenzoic acidHCID 65578Oxalyl chlorideHCID 867033695-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

Produkt 1

HCID 725501905-(4-Acetamidobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamideAusbeute 3,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-acetamidobenzoic acid (0.204 g, 1.14 mmol) and a catalytic amount of DMF in dry THF (15 mL) was added dropwise oxalyl chloride (0.2 mL, 2.30 mmol) at 0° C., and the mixture was stirred for 2 hrs at rt. The solvent was evaporated, and the residual oxalyl chloride was removed with azeotropic distillation using toluene under nitrogen atmosphere 4 times. The resulting acid chloride was then dissolved in pyridine (6 mL) and cooled to 0° C. To this solution, a solution of 5-amino-2-(naphthalene-2-ylamino)thiazole-4-carboxamide (0.27 g, 0.95 mmol) in pyridine (6 mL) was added at 0° C., and the mixture was stirred for 12 hrs at rt. The solvent was evaporated, and the residue was suspended into 1M HCl, and the resulting solids were collected and dried. The crude solids were purified by silica gel column chromatography eluted with 3% MeOH in DCM to give 16 mg (3.7% yield) of the titled compound.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residual oxalyl chloride was removed with azeotropic distillation
  3. dissolutionThe resulting acid chloride was then dissolved in pyridine (6 mL)
  4. temperaturecooled to 0° C
  5. stirringthe mixture was stirred for 12 hrs at rt
  6. customThe solvent was evaporated
  7. customthe resulting solids were collected
  8. customdried
  9. customThe crude solids were purified by silica gel column chromatography
  10. washeluted with 3% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-c13016e109f74b5685cdecd8c377eded
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102637B2

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