Dichloromethane methanol → HCID 76182138, compound

HRID 1091596Notes

Reaction equation

HRID 1091596 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:40])[C:15]([O:32]CC2C=CC=CC=2)=[C:16]2[C:29](=[O:30])[N:20]3[CH:21]4[CH2:28][CH2:27][CH2:26][CH2:25][CH:22]4[CH2:23][O:24][CH:19]3[CH2:18][N:17]2[CH:31]=1)=[O:12].[H][H].CO.ClCCl>O1CCCC1.[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:40])[C:15]([OH:32])=[C:16]2[C:29](=[O:30])[N:20]3[CH:21]4[CH2:28][CH2:27][CH2:26][CH2:25][CH:22]4[CH2:23][O:24][CH:19]3[CH2:18][N:17]2[CH:31]=1)=[O:12]

Participants

6

Reactant 3

HCID 21226129Dichloromethane methanolHCID 77150779HCID 77150779, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 76182138HCID 76182138, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

racemic-(4aR,6aR,14aS)—N-[(2,4-Difluorophenyl)methyl]-11,13-dioxo-12-[(phenylmethyl)oxy]-1,3,4,4a,5,6a,7,11,13,14a-decahydro-2H-pyrido[1′,2′:4,5]pyrazino[1,2-a][3,1]benzoxazine-10-carboxamide (13 mg, 0.0236 mmol) was dissolved in tetrahydrofuran and 10 w.t. % Pd/C (13 mg) was added. Hydrogen was passed through the solution several times and the mixture was stirred at 1 atm hydrogen for 18 hours until the reaction was determined complete by TLC (5% methanol/dichloromethane). The mixture was filtered through Celtite, eluting with methanol/chloroform and the filtrate was concentrated under reduced pressure and purified by HPLC to yield the title compound (7.3 mg, 73%)1H NMR (CDCl3) δ 12.45 (m, 1H), 10.38 (s, 1H), 8.30 (s, 1H), 7.32 (m, 1H), 6.83-6.76 (m, 2H), 5.23 (m, 1H), 4.75 (m, 1H), 4.63 (m, 2H), 4.26 (m, 1H), 4.12-4.01 (m, 2H), 3.83 (m, 1H), 2.30 (m, 1H), 1.91 (m, 1H), 1.80 (m, 1H), 1.67-1.40 (m, 5H), 1.20 (m, 1H); ES+ MS: 460 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celtite
  2. washeluting with methanol/chloroform
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-dd841ee4c7ee4fc5ae1c9b0eaf1cd2a7
Source dataset
uspto-grants-2012_03
Patent number
US08129385B2

Reaction notes

Loading…