1,2-Dichloroethane → 7-[(3R)-3-[(1,1-Dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(ethylthio)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 1272383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1272383
Cl.[CH2:2]([S:4][C:5]1[N:6]=[CH:7][C:8]2[CH2:14][CH2:13][NH:12][CH2:11][C:9]=2[N:10]=1)[CH3:3].[CH3:15][C:16]([CH3:36])([O:18][C:19]([NH:21][C@H:22]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[F:35])[CH2:23][C:24](O)=[O:25])=[O:20])[CH3:17].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:17][C:16]([CH3:36])([O:18][C:19]([NH:21][C@H:22]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[F:35])[CH2:23][C:24]([N:12]1[CH2:13][CH2:14][C:8]2[CH:7]=[N:6][C:5]([S:4][CH2:2][CH3:3])=[N:10][C:9]=2[CH2:11]1)=[O:25])=[O:20])[CH3:15]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11347588(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acidHCID 184565142-(Ethylthio)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride

Produkt 1

HCID 690254087-[(3R)-3-[(1,1-Dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(ethylthio)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 47 mg (0.19 mmol) of 2-(ethylthio)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride, 59 mg (0.19 mmol) of (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid, 37 mg (0.19 mmol) of EDC, 26 mg (0.19 mmol) of HOBt, and 0.15 mL (0.57 mmol) of diisopropylethylamine in 1.5 mL of dichloromethane was stirred at ambient temperature overnight. The mixture was subjected directly to purification by flash chromatography (5 g silica gel cartridge, 20-to-50% ethyl acetate/hexane step gradient) to give 85 mg (91%) of the title compound as a white solid.

Aufarbeitung

  1. customThe mixture was subjected directly to purification by flash chromatography (5 g silica gel cartridge, 20-to-50% ethyl acetate/hexane step gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e12eef5478f64e57aa74365249330e0b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208498B2

Notizen zur Reaktion

Wird geladen…