Diisopropylethylamine → 4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-N-pyrrolidin-1-yl-benzamide

HRID 1783400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783400
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.CCN(C(C)C)C(C)C.Cl.[NH2:63][N:64]1[CH2:68][CH2:67][CH2:66][CH2:65]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:63][N:64]3[CH2:68][CH2:67][CH2:66][CH2:65]3)=[O:29])=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 686243374-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid

Produkt 1

HCID 160354754-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-N-pyrrolidin-1-yl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid (50 mg, 0.10 mmol) was dissolved in DMF (1 ml) and activated with the coupling reagent TPTU (33 mg, 0.11 mmol) and Hünig's base (0.03 ml, 0.26 mmol) for 2 min. 1-Aminopyrrolidine hydrochloride (0.013 g, 0.22 mmol) and further Hünig's base (0.03 ml, 0.26 mmol were added. After 1 h the reaction mixture was concentrated under reduced pressure and the residue taken up in ethyl acetate and washed with 5% KHSO4/10% K2SO4 (2×), water, brine, dried (MgSO4), filtered, concentrated under reduced pressure and purified over silica gel (ethyl acetate->ethyl acetate/5% MeOH) and the purified product was lyophilized: white lyophilisate 32 mg;

Aufarbeitung

  1. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  2. washwashed with 5% KHSO4/10% K2SO4 (2×), water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified over silica gel (ethyl acetate->ethyl acetate/5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-903a00b6940a4f14a328e8c3828555f4
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501406B2

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