Benzyl Bromide → Benzyl rel-({(3r,4r)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetate

HRID 564413

Reaktionsgleichung

Reaktionsgleichung von HRID 564413
[CH2:1]([O:8][C@@H:9]1[CH2:13][N:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:16][CH2:15]2)[CH2:11][C@H:10]1[NH:28][C:29](=[O:44])[CH2:30][NH:31][C:32](=[O:43])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=1)C1C=CC=CC=1.BrC[C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48].C(Br)C1C=CC=CC=1.C(NC(=O)[O-])C1C=CC=CC=1>CO.[Pd]>[CH3:27][O:26][C:23]1[N:22]=[CH:21][C:20]([N:17]2[CH2:16][CH2:15][CH:14]([N:12]3[CH2:11][C@@H:10]([NH:28][C:29](=[O:44])[CH2:30][NH:31][C:32](=[O:43])[C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:42])[F:41])[CH:34]=4)[C@H:9]([O:8][CH2:1][C:47]([O:49][CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:48])[CH2:13]3)[CH2:19][CH2:18]2)=[CH:25][CH:24]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 62576Benzyl bromoacetateHCID 22253685N-benzylcarbamateHCID 67005044Rel-n-[2-({(3r,4r)-4-(benzyloxy)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Produkt 1

HCID 67004369Benzyl rel-({(3r,4r)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was synthesized in similar fashion to rel-N-[2-({(3R,4R)-4-(benzyloxy)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide, benzyl bromoacetate was substituted for benzyl bromide, as well as benzylcarbamate deprotection was accomplished with H2 gas (1 atm), 10% Palladium/Carbon in methanol, and was isolated as a white solid. 1H-NMR (CD3OD) δ: 1.17-1.25 (m, 1H), 1.50-1.67 (m, 2H), 1.80-1.94 (m, 2H), 2.13-2.25 (m, 1H), 2.44 (dd, J=10.5, 4.2 Hz, 1H), 2.61-2.74 (m, 3H), 2.84 (dd, J=9.9, 6.0 Hz, 1H), 3.25 (dd, J=10.2, 6.3 Hz, 1H), 3.35-3.46 (m, 3H), 3.85 (s, 3H), 3.82-3.93 (m, 1H), 4.05-4.14 (m, 3H), 4.18-4.29 (m, 3H), 5.11 (s, 2H), 6.63 (d, J=9.0 Hz, 1H), 6.74 (d, J=7.8 Hz, 1H), 7.20-7.38 (m, 5H), 7.51 (t, J=7.8 Hz, 1H), 7.70-7.75 (m, 2H), 7.96 (d, 7.8 Hz, 1H), 8.06 (s, 1H). MS m/z: 670 (M+1).

Aufarbeitung

  1. customwas isolated as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-3cea12a4628e40ce9e237a7129b91cd9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067457B2

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