HCID 58015327, compound → HCID 54713646, compound

HRID 2171760Notes

Reaction equation

HRID 2171760 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([C:13]1[C:14](=[O:38])[C:15]([O:30]CC2C=CC=CC=2)=[C:16]2[C:21](=[O:22])[N:20]3[CH2:23][C@@H:24]4[CH2:28][CH2:27][CH2:26][N:25]4[C@H:19]3[CH2:18][N:17]2[CH:29]=1)=[O:12]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([C:13]1[C:14](=[O:38])[C:15]([OH:30])=[C:16]2[C:21](=[O:22])[N:20]3[CH2:23][C@@H:24]4[CH2:28][CH2:27][CH2:26][N:25]4[C@H:19]3[CH2:18][N:17]2[CH:29]=1)=[O:12]

Participants

4

Reactant 1

HCID 58015327HCID 58015327, compound

Product 1

HCID 54713646HCID 54713646, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4aR,13aS)—N-[(2,4-difluorophenyl)methyl]-9,11-dioxo-10-[(phenylmethyl)oxy]-2,3,4a,5,9,11,13,13a-octahydro-1H-pyrido[1,2-a]pyrrolo[1′,2′:3,4]imidazo[1,2-d]pyrazine-8-carboxamide (19 mg, 0.04 mmol) in methanol (8 mL) was added 10% Pd/C (10 mg). Hydrogen was bubbled through the reaction mixture via a balloon for 2 h. The resultant mixture was filtered through Celite with methanol and dichloromethane. The filtrate was concentrated in vacuo to give the title compound (6 mg, 38%) as a white solid. 1H NMR (CDCl3) δ 11.73 (m, 1H), 10.36 (m, 1H), 8.31 (s, 1H), 7.33 (m, 1H), 6.78 (m, 2H), 4.62 (m, 2H), 4.50 (m, 1H), 4.27-4.19 (m, 2H), 3.87-3.77 (m, 2H), 3.16-3.08 (m, 2H), 2.83 (m, 1H): 2.11-1.65 (m, 4H); ES+ MS: 431 (M+1).

Workup

  1. customHydrogen was bubbled through the reaction mixture via a balloon for 2 h
  2. filtrationThe resultant mixture was filtered through Celite with methanol and dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-84ed98ee501a4c6dba00d0dc06d4a803
Source dataset
uspto-grants-2015_06
Patent number
US09051337B2

Reaction notes

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