Hydrochloric Acid → (Pyrrolidine-1-carbonyl)sulfamic acid 3-[3-tert-butyl-5-(3-naphthalen-1-yl-ureido)-pyrazol-1-yl]phenyl ester

HRID 1392302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392302
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[C:13]([C:17]1[CH:21]=[C:20]([NH:22][C:23]([NH:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[O:24])[N:19]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[CH:37]=2)[N:18]=1)([CH3:16])([CH3:15])[CH3:14].Cl.[Na+].[Cl-]>C(Cl)Cl>[C:13]([C:17]1[CH:21]=[C:20]([NH:22][C:23]([NH:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[O:24])[N:19]([C:36]2[CH:37]=[C:38]([O:42][S:2](=[O:4])(=[O:3])[NH:5][C:6]([N:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])[CH:39]=[CH:40][CH:41]=2)[N:18]=1)([CH3:16])([CH3:14])[CH3:15]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 31268PyrrolidineHCID 70918Chlorosulfonyl isocyanateHCID 218673141-[3-Tert-butyl-1-(3-hydroxyphenyl)-1h-pyrazol-5-yl]-3-(naphthalene-1-yl)urea

Produkt 1

HCID 25226698(Pyrrolidine-1-carbonyl)sulfamic acid 3-[3-tert-butyl-5-(3-naphthalen-1-yl-ureido)-pyrazol-1-yl]phenyl esterAusbeute 1,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirring solution of chlorosulfonyl isocyanate (0.35 g, 5 mmol) in CH2Cl2 (20 mL) at 0° C. was added pyrrolidine (0.18 g, 5 mmol) at such a rate that the reaction temperature did not rise above 5° C. After stirring for 2 h, a solution of Example 41 (1.10 g, 6.5 mmol) and triethylmine (0.46 g, 9 mmol) in CH2Cl2 (20 mL) was added. When the addition was complete, the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was poured into 10% HCl (10 mL) saturated with NaCl , the organic layer was separated and the aqueous layer extracted with ether (20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo, purified by preparative HPLC to yield (pyrrolidine-1-carbonyl)sulfamic acid 3-[3-tert-butyl-5-(3-naphthalen-1-yl-ureido)-pyrazol-1-yl]phenyl ester (40 mg). 1H NMR (CDCl3): δ 9.12 (brs, 1H), 8.61 (brs, 1H), 7.85-7.80 (m, 3H), 7.65 (d, J=8.0 Hz, 2H), 7.53-7.51 (m, 1H), 7.45-7.25 (m, 5H), 6.89 (s, 4H), 3.36-3.34 (brs, 1H), 3.14-3.13 (brs, 2H), 1.69 (brs, 2H), 1.62 (brs, 2H), 1.39 (s, 9H); MS (ESI) m/z: 577 (M+H+).

Aufarbeitung

  1. customdid not rise above 5° C
  2. additionWhen the addition
  3. stirringstirred overnight
  4. customthe organic layer was separated
  5. extractionthe aqueous layer extracted with ether (20 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6665831a07374f2281ef566f98f70090
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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