HCID 66594302, compound → HCID 54713700, compound

HRID 920692Notes

Reaction equation

HRID 920692 reaction equation
OC1C(=O)C(C(N)=O)=CN2CC3N4CCCCC4CN3C(=O)C=12.[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[CH2:32][NH:33][C:34]([C:36]1[C:37](=[O:62])[C:38]([O:54]CC2C=CC=CC=2)=[C:39]2[C:44](=[O:45])[N:43]3[CH2:46][C@@H:47]4[CH2:52][CH2:51][CH2:50][CH2:49][N:48]4[C@@H:42]3[CH2:41][N:40]2[CH:53]=1)=[O:35]>[Pd]>[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[CH2:32][NH:33][C:34]([C:36]1[C:37](=[O:62])[C:38]([OH:54])=[C:39]2[C:44](=[O:45])[N:43]3[CH2:46][C@@H:47]4[CH2:52][CH2:51][CH2:50][CH2:49][N:48]4[C@@H:42]3[CH2:41][N:40]2[CH:53]=1)=[O:35]

Participants

4

Reactant 2

HCID 66594302HCID 66594302, compoundHCID 131734888HCID 131734888, compound

Product 1

HCID 54713700HCID 54713700, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(5aS,14aS)-N-[(2,4-Difluorophenyl)ethyl)methyl]-11-hydroxy-10,12-dioxo-1,2,3,4,5a,6,10,12,14,14a-decahydropyrido[1,2-a]pyrido[1′,2′:3,4]imidazo[1,2-d]pyrazine-9-carboxamide. In a manner similar to that described in example Z-37, from (5aS,14aS)-N-[(2,4-difluorophenyl)methyl]-10,12-dioxo-11-[(phenylmethyl)oxy]-1,2,3,4,5a,6,10,12,14,14a-decahydropyrido[1,2-a]pyrido[1′,2′:3,4]imidazo[1,2-d]pyrazine-9-carboxamide (18 mg, 0.0337 mmol) and 10 w.t.% Pd/C (catalytic amount) was prepared the title compound as a white solid (13 mg, 87%) after purification by HPLC, 1H NMR (CDCl3) δ 11.71 (br s, 1H), 10.36 (br s, 1H), 8.31 (s, 1H), 7.34 (m, 1H), 6.78 (m, 2H), 4.64-4.57 (m, 2H), 4.28 (m, 1H), 4.12 (m, 1H), 3.92-3.89 (m, 2H), 3.22 (m, 1H), 3.04 (m, 1H), 2.49 (m, 1H), 2.28 (m, 1H), 1.97-1.89 (m, 2H), 1.78 (m, 1H), 1.66-1.60 (m, 2H), 1.43-1.36 (m, 2H); ES+MS: 445 (M+1).

Sources & evidence

ORD record
ord-213049e35fd04f0a8d7787f67035b69b
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

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