HCID 77150664, compound → HCID 76182140, compound

HRID 1622936Notes

Reaction equation

HRID 1622936 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:46])[C:15]([O:38]CC2C=CC=CC=2)=[C:16]2[C:35](=[O:36])[N:20]3[CH:21]4[CH2:28][CH2:27][CH:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:25][CH:22]4[CH2:23][O:24][CH:19]3[CH2:18][N:17]2[CH:37]=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:46])[C:15]([OH:38])=[C:16]2[C:35](=[O:36])[N:20]3[CH:21]4[CH2:28][CH2:27][CH:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:25][CH:22]4[CH2:23][O:24][CH:19]3[CH2:18][N:17]2[CH:37]=1)=[O:12]

Participants

4

Reactant 1

HCID 77150664HCID 77150664, compound

Product 1

HCID 76182140HCID 76182140, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

racemic-(3S,4aR,6aR,14aS)—N-[(2,4-Difluorophenyl)methyl]-11,13-dioxo-3-phenyl-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 (27 mg, 0.0432 mmol) was suspended in methanol, 10 w.t, % Pd/C (3 mg) was added and hydrogen was bubbled through the system several times until the reaction was determined complete by TLC (5% methanol/dichloromethane). The suspension was filtered through Celite eluting with methanol/chloroform and the filtrate was concentrated under reduced pressure and purified by HPLC to give the title compound (13 mg, 57%) as a white solid, 1H NMR (CDCl3) δ 12.40 (br s, 1H), 10.37 (m, 1H), 8.32 (s, 1H), 7.37-7.28 (m, 3H), 7.24-7.15 (m, 4H), 6.79 (m, 2H), 5.78 (br s, 1H), 4.85 (m, 1H), 4.62 (m, 2H), 4.29 (m, 1H), 4.16-4.09 (m, 2H), 3.92 (dd, J=11.6, 4.8 Hz, 1H), 2.58 (m, 1H), 2.46 (m, 1H), 2.07-1.64 (m, 7H); ES+ MS: 536 (M+1).

Workup

  1. customhydrogen was bubbled through the system several times until the reaction
  2. filtrationThe suspension was filtered through Celite
  3. washeluting with methanol/chloroform
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-9b04fa1febba4082a732fad8fe61e23a
Source dataset
uspto-grants-2014_07
Patent number
US08778943B2

Reaction notes

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