1,2-Dichloroethane → N-[(1R)-1-[(Benzylsulfonyl)methyl]-2-{[(1S)-1-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}ethyl]amino}-2-oxoethyl]morpholine-4-carboxamide

HRID 15276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15276
[N:1]1([C:7]([NH:9][C@@H:10]([CH2:14][S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C:11]([OH:13])=O)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:25][C:26]([F:40])([F:39])[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH2:35][C@@H:36]([NH2:38])[CH3:37])=[CH:30][CH:29]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:37][C@H:36]([NH:38][C:11]([C@@H:10]([NH:9][C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:8])[CH2:14][S:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:13])[CH2:35][NH:34][C:31]1[CH:30]=[CH:29][C:28]([O:27][C:26]([F:25])([F:39])[F:40])=[CH:33][CH:32]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11439693(R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acidHCID 59733160HCID 59733160, Verbindung

Produkt 1

HCID 9547980N-[(1R)-1-[(Benzylsulfonyl)methyl]-2-{[(1S)-1-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}ethyl]amino}-2-oxoethyl]morpholine-4-carboxamideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(R)-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (73 mg, 0.21 mmol, 1.0 eq.), N1-(4-Trifluoromethoxy-phenyl)-(S)-propane-1,2-diamine from Scheme 1a (48 mg, 0.21 mmol, 1.0 eq.), EDC (59 mg, 0.31 mmol, 1.5 eq.), and HOBT (38 mg, 0.25 mmol, 1.2 eq.) were dissolved in CH2Cl2 at room temperature. N-methylmorpholine (225 μL, 2.05 mmol, 10 eq.) was added via syringe and the reaction was monitored to completion by LC/MS. The solvent was evaporated and the reaction was purified by mass-directed HPLC and provided 44 mg (0.06 mmol, 31%) of a off-white solid as a mono-TFA salt: HPLC-MS calcd. for C25H31F3N4O6S (M+H+) 573.2, found 573.3.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe reaction was purified by mass-directed HPLC

Quellen und Nachweise

ORD-Eintrag
ord-449aa6a20fd44ecc966ad0b9e603531a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732449B2

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