1-Methylcyclopropanecarboxylic acid → (8aS)-7-[(1-Methylcyclopropyl)carbonyl]-2-[(1S,2R)-2-phenylcyclopropyl]tetrahydro imidazo[1,5-a]pyrazine-1,3(2H,5H)-dione

HRID 1260479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260479
ClC1C(Cl)=CC=CC=1N[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:18](=[O:31])[N:19]([C@H:22]3[CH2:24][C@@H:23]3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:21])[C@@H:14]2[CH2:13]1)=[O:11].Cl.[C:33]1([C@H:39]2[CH2:41][C@@H:40]2N2C(=O)[C@@H]3CNCCN3C2=O)C=CC=CC=1.CC1(C(O)=O)CC1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:33][C:39]1([C:10]([N:12]2[CH2:17][CH2:16][N:15]3[C:18](=[O:31])[N:19]([C@H:22]4[CH2:24][C@@H:23]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:20](=[O:21])[C@@H:14]3[CH2:13]2)=[O:11])[CH2:41][CH2:40]1

Komponenten

7

Edukt 5

HCID 813261-Methylcyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 56676510(8aS)-N-(2,3-dichlorophenyl)-1,3-dioxo-2-[(1S,2R)-2-phenylcyclopropyl]-5,6,8,8a-tetrahydroimidazo[1,5-a]pyrazine-7-carboxamideHCID 67300061(8aS)-2-[(1S,2R)-2-Phenylcyclopropyl]tetrahydroimidazo[1,5-a]pyrazine-1,3(2H,5H)-dione HCl salt

Produkt 1

HCID 67300208(8aS)-7-[(1-Methylcyclopropyl)carbonyl]-2-[(1S,2R)-2-phenylcyclopropyl]tetrahydro imidazo[1,5-a]pyrazine-1,3(2H,5H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 0.2 M solution of Example 4, D2 (1 eq) in DMF were added 1-methylcyclopropanecarboxylic acid (1.1 eq), DIPEA (2.5 eq) and TBTU (1.5 eq). The reaction mixture was stirred at RT for 12 h. The crude product was purified by preparative RP-HPLC using H2O (0.1% TFA) and MeCN (0.1% TFA) as eluents, affording the title compound. 1H NMR (300 MHz, DMSO-d6, 300K) δ: 7.27-7.09 (5H, m), 4.42-4.32 (1H, m), 4.19 (1H, d, J=9.3 Hz), 4.05-3.95 (1H, m), 3.91-3.82 (1H, m), 2.97-2.81 (3H, m), 2.65-2.57 (1H, m), 2.36-2.26 (1H, m), 1.49-1.40 (1H, m), 1.39-1.30 (1H, m), 1.18 (3H, s), 0.83-0.76 (2H, m), 0.54-0.48 (2H, m). MS (ES) C20H23N3O3 requires: 353, found: 354 (M+H)+.

Aufarbeitung

  1. customThe crude product was purified by preparative RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-230487b326064c39a6be4746e0b29275
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470823B2

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