(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester → 2-[4-(4-Ureido-phenyl)-thiazol-2-yl carbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 737173
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[Si]([N:41]=[C:42]=[O:43])(C)(C)C>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:30])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:42]([NH2:41])=[O:43])=[CH:27][CH:28]=2)[N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 86616427(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester2×HCID 86616432dioxane TMS isocyanate

Produkt 1

HCID 591409232-[4-(4-Ureido-phenyl)-thiazol-2-yl carbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5050, Example 50, 40 mg, 0.095 mmol) was dissolved in 4 ml of 1:1 dioxane/TMS isocyanate. Reaction mixture was heated at 70° C. for 7 hours. It was then evaporated to dryness. The crude was redissolved in 10 ml of DMF and purified on reverse phase HPLC. MS: 466.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 12.39 (d, 1H), 7.72 (d, 2H), 7.42 (d, 3H), 7.35 (s, 2H), 7.10 (dd, 2H), 5.88 (br s, 2H), 5.02 (m, 2H), 4.50 (m, 1H), 2.25 (m, 2H), 1.90 (m, 4H).

Aufarbeitung

  1. customReaction mixture
  2. customIt was then evaporated to dryness
  3. dissolutionThe crude was redissolved in 10 ml of DMF
  4. custompurified on reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9bf98091e533456692eb761d3b5c0e78
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595398B2

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