Triethylsilane → 4-Fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acid

HRID 1985764

Reaktionsgleichung

Reaktionsgleichung von HRID 1985764
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH:13]=O)=[CH:11][N:12]=1.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[F:25])[C:19]([OH:21])=[O:20].C([SiH](CC)CC)C>C(Cl)Cl>[F:25][C:24]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=1[NH:15][CH2:13][C:10]1[S:9][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 12052TriethylsilaneHCID 753963-Amino-4-fluorobenzoic acidHCID 220190582-(Pyridin-2-ylamino)thiazole-5-carbaldehyde2×

Produkt 1

HCID 220190564-Fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acidAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(pyridin-2-ylamino)-thiazole-5-carbaldehyde (1.0 g, 4.90 mmol, compound 1A) in methylene chloride (20 mL) at RT 3-amino-4-fluorobenzoic acid (0.95 g, 4.90 mmol) TFA (5 mL) and triethylsilane (1.71 mg, 14.7 mmol) were added. The above reaction mixture was stirred at RT for 4 h, then concentrated in vacuo and the resulting slurry was triturated with methanol to afford 4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acid as light yellow solid (1.54 g, 91%) (M+H)+=345.

Aufarbeitung

  1. additionwere added
  2. customThe above reaction mixture
  3. concentrationconcentrated in vacuo
  4. customthe resulting slurry was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-9feb685a2c5e4825859ad868702b2ffd
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547711B2

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