HCID 66594505, compound → HCID 76182071, compound

HRID 1622945Notes

Reaction equation

HRID 1622945 reaction equation
Cl.N[C@H]1CCCC[C@H]1CNC.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH:21][C:22]([C:24]1[C:25](=[O:52])[C:26]([O:44]CC2C=CC=CC=2)=[C:27]2[C:41](=[O:42])[N:31]3[CH:32]4[CH:37]([CH2:38][N:39]([CH3:40])[CH:30]3[CH2:29][N:28]2[CH:43]=1)[CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:23]>[Pd]>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH:21][C:22]([C:24]1[C:25](=[O:52])[C:26]([OH:44])=[C:27]2[C:41](=[O:42])[N:31]3[CH:32]4[CH:37]([CH2:38][N:39]([CH3:40])[CH:30]3[CH2:29][N:28]2[CH:43]=1)[CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:23]

Participants

4

Reactant 2

HCID 66594505HCID 66594505, compoundHCID 77150780HCID 77150780, compound2×

Product 1

HCID 76182071HCID 76182071, compoundYield 630.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a manner similar to that described in example Z-35, from racemic-{[(1S,2S)-2-aminocyclohexyl]methyl}methylamine hydrochloride (46 mg, 0.215 mmol) and 16a (35 mg, 0.0744 mmol) was prepared racemic-(4aS,6aS,14aS)—N-[(2,4-difluorophenyl)methyl]-6-methyl-11,13-dioxo-12-[(phenylmethyl)oxy]-1,2,3,4,4a,5,6,6a,7,11,13,14a-dodecahydropyrido[1′,2′:4,5]pyrazino[1,2-a]quinazoline-10-carboxamide (1.7 mg, 41%) as a white solid. This material was deprotected in s second step similar to the procedure described in example Z-37. Thus, from racemic-(4aS,6aS,14aS)—N-[(2,4-difluorophenyl)methyl]-6-methyl-11,13-dioxo-12-[(phenylmethyl)oxy]-1,2,3,4,4a,5,6,6a,7,11,13,14a-dodecahydropyrido[1′,2′:4,5]pyrazino[1,2-a]quinazoline-10-carboxamide (17 mg, 0.0302 mmol) and 10% Pd/C (1 mg) was prepared the title compound as a white solid (9 mg, 64%), 1H NMR (CDCl3) 10.44 (m, 1H), 8.29 (s, 1H), 7.34 (m, 1H), 6.79 (m, 2H), 4.78 (m, 1H), 4.62 (br s, 2H), 4.29 (br s, 2H), 3.41 (s, 1H), 2.92 (m, 1H), 2.66 (m, 1H), 2.35-2.25 (m, 4H), 1.90-1.74 (m, 2H), 1.67-1.24 (m, 6H); ES+ MS: 473 (M+1).

Sources & evidence

ORD record
ord-5afce875b6654eb396481243fd2c2e8e
Source dataset
uspto-grants-2014_07
Patent number
US08778943B2

Reaction notes

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