HCID 77150689, compound → HCID 129307510, compound

HRID 920693Notes

Reaction equation

HRID 920693 reaction equation
Cl.CC(C)CNCC1CCCC1N.[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[CH2:22][NH:23][C:24]([C:26]1[C:27](=[O:56])[C:28]([O:48]CC2C=CC=CC=2)=[C:29]2[C:45](=[O:46])[N:33]3[CH:34]4[CH2:44][CH2:43][CH2:42][CH:35]4[CH2:36][N:37]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH:32]3[CH2:31][N:30]2[CH:47]=1)=[O:25]>[Pd]>[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[CH2:22][NH:23][C:24]([C:26]1[C:27](=[O:56])[C:28]([OH:48])=[C:29]2[C:45](=[O:46])[N:33]3[CH:34]4[CH2:44][CH2:43][CH2:42][CH:35]4[CH2:36][N:37]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH:32]3[CH2:31][N:30]2[CH:47]=1)=[O:25]

Participants

4

Reactant 2

HCID 77150689HCID 77150689, compoundHCID 77150703HCID 77150703, compound

Product 1

HCID 129307510HCID 129307510, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a manner similar to that described in example Z-35, from racemic-(1S,2S)-2-{[(2-methylpropyl)amino]methyl}cyclopentanamine hydrochloride 105 mg, 0.434 mmol) and 16a (56 mg, 0.119 mmol) was prepared racemic-(3aS,5aS,13aS)-N-[(2,4-difluorophenyl)methyl]-5 (2-methylpropyl)-10,12-dioxol-11-[(phenylmethyl)oxy]-2,3,3a,4,5,5a,6,10,12,13a-decahydro-1H-cyclopenta[e]pyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-9-carboxamide (62 mg, 74%). This material was deprotected in a second step similar to the procedure described in example Z-37. Thus, from racemic-(3aS,5aS,13aS)-N-[(2,4-difluorophenyl)methyl]-5-(2-methylpropyl)-10,12-dioxo-11-[(phenylmethyl)oxy]2,3,3a,4,5,5a,6,10,12,13a-decahydro-1H-cyclopenta[e]pyrido[1′,2′:4,5]pyrazino[1,2-a]pyrimidine-9-carboxamide (48 mg, 0.081 mmol) and 10% Pd/C (catalytic amount), the title compound was prepared as a white solid after purification by HPLC (80 mg, 75%). 1H NMR (CDCl3) 12.69 (s, 1H), 10.42 (s, 1H), 828 (s, 1H), 7.34 (m, 1H), 6.79 (m, 2H), 4.83 (s, 1H), 4.68-4.58 (m, 3H), 4.29 (m, 1H), 4.14 (m, 1H), 2.01 (m, 1H), 2.46-2.82 (m, 3H), 2.16-2.09 (m, 2H), 1.85-1.61 (m, 5H), 1.39 (m, 1H), 0.88 (m, 6H); ES+MS: 501 (M+1).

Workup

  1. customafter purification by HPLC (80 mg, 75%)

Sources & evidence

ORD record
ord-87a166e29c8d4e2793a71021f8aba804
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

Loading…