HCID 86617478, compound → HCID 54692286, compound

HRID 1162832Notes

Reaction equation

HRID 1162832 reaction equation
OC(C(F)(F)F)=O.C([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH:16]1[CH2:21][N:22]1[C:27](=[O:28])[C:26]([OH:29])=[C:25]2[C:30](=[O:42])[N:31]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH2:32][CH2:33][N:24]2[C:23]1=[O:43])C1C=CC=CC=1>C(O)C.[Pd]>[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][N:31]2[CH2:32][CH2:33][N:24]3[C:23](=[O:43])[N:22]([CH2:21][CH:16]4[CH2:17][O:18][CH2:19][CH2:20][NH:15]4)[C:27](=[O:28])[C:26]([OH:29])=[C:25]3[C:30]2=[O:42])=[CH:40][CH:39]=1

Participants

4

Reactant 1

HCID 86617478HCID 86617478, compound

Product 1

HCID 54692286HCID 54692286, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-[(4-Benzylmorpholin-3-yl)methyl]-2-(4-fluorobenzyl)-9-hydroxy-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione TFA salt (921 mg, 1.86 mmol, from Example 16) was dissolved in degassed ethanol (10 mL) under nitrogen and 10% palladium on carbon (92 mg) was added. The flask was evacuated and purged with hydrogen three times using a vacuum line and a hydrogen gas balloon. The reaction was stirred overnight under a hydrogen gas atmosphere. The reaction was filtered through a thin pad of celite, washing with degassed ethanol. The filtrate was concentrated to a yellow solid which was triturated with methanol. The solids were collected by vacuum filtration to give the desired product as a white powder. 1H NMR (400 MHz, d6 DMSO) δ 11.9 (s, 1H), 8.96 (bs, 2H), 7.39 (m, 2H), 7.22 (m, 2H), 4.72 (s, 2H), 4.13 (m, 1H), 3.84-4.02 (m, 5H), 3.52-3.70 (m, 5H), 3.27 (m, 1H), and 3.05 (m, 1H). HRMS (FT-ICR C19H21FN4O5+H)=405.1572; calculated 405.1569.

Workup

  1. customThe flask was evacuated
  2. custompurged with hydrogen three times
  3. filtrationThe reaction was filtered through a thin pad of celite
  4. washwashing with degassed ethanol
  5. concentrationThe filtrate was concentrated to a yellow solid which
  6. customwas triturated with methanol
  7. filtrationThe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-88ce79826abb4235b140e28d1d9b7f20
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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