Phthalimide → HCID 11330005, compound

HRID 2373911Notes

Reaction equation

HRID 2373911 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:31][C:32]1[C:33]2[N:34]([C:38]([CH:57]3[CH2:60][CH2:59][CH2:58]3)=[N:39][C:40]=2[C:41]2[CH:42]=[C:43]([CH:54]=[CH:55][CH:56]=2)[O:44][CH2:45][C:46]2[CH:47]=[C:48]([CH2:52]O)[CH:49]=[CH:50][CH:51]=2)[CH:35]=[CH:36][N:37]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:31][C:32]1[C:33]2[N:34]([C:38]([CH:57]3[CH2:60][CH2:59][CH2:58]3)=[N:39][C:40]=2[C:41]2[CH:42]=[C:43]([CH:54]=[CH:55][CH:56]=2)[O:44][CH2:45][C:46]2[CH:47]=[C:48]([CH:49]=[CH:50][CH:51]=2)[CH2:52][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH:35]=[CH:36][N:37]=1

Participants

6

Reactant 4

HCID 6809Phthalimide2×HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate2×HCID 11418161HCID 11418161, compound

Product 1

HCID 11330005HCID 11330005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phthalimide (44 mg, 0.25 mmol), PS-triphenylphosphine (169 mg, 0.37 mmol) and {3-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxymethyl]-phenyl}-methanol (100 mg, 0.25 mmol) were added to a dry rbf and dissolved with THF (1.25 mL), which was then evacuated and purged three times with nitrogen. DIAD (61 mg, 0.30 mmol) was added slowly to the reaction mixture and allowed to slowly stir for 24 h at rt. LC/MS analysis indicated that the reaction was nearly finished with some starting material left, but mostly product. Therefore, 0.2 eq. of DIAD and phthalimide were added and the reaction was left to proceed. The reaction mixture was filtered through a glass frit and washed with CH2Cl2 multiple times. The filtrate was concentrated to a red/brown oil and purified using silica gel column chromatography (1% NH3 in MeOH:CH2Cl2) to afford the title compound; 1H NMR (CDCl3, 400 MHz) δ 2.00-2.09 (m, 1H), 2.11-2.23 (m, 1H), 2.45-2.53 (m, 2H), 2.59-2.69 (m, 2H), 3.77-3.85 (m, 1H), 4.87 (s, 2H), 5.11 (s, 2H), 6.99-7.02 (m, 2H), 7.10 (d, J=5.2 Hz, 1H), 7.23-7.26 (m, 2H), 7.35-7.42 (m, 4H), 7.49 (s, 1H), 7.69-7.73 (m, 2H), 7.82-7.87 (m, 2H); MS (ES+): m/z 530.14 (100) [MH+].

Workup

  1. customwas then evacuated
  2. custompurged three times with nitrogen
  3. waitleft
  4. waitthe reaction was left
  5. filtrationThe reaction mixture was filtered through a glass frit
  6. washwashed with CH2Cl2 multiple times
  7. concentrationThe filtrate was concentrated to a red/brown oil
  8. custompurified

Sources & evidence

ORD record
ord-076cabf4fcbe4e86be0d4c5bd46f50c9
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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