Phthalimide → HCID 66780004, compound

HRID 1958056Notes

Reaction equation

HRID 1958056 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C(O[CH2:17][C:18]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[C:26]=2[CH3:35])[C:22]2[N:36]=[C:37]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[S:38][C:21]=2[C:20](=[O:45])[N:19]=1)(=O)C.[C:46]1(=[O:56])[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48](=[O:55])[NH:47]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:35][C:26]1[C:27]([C:31]([F:32])([F:33])[F:34])=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][N:23]1[C:22]2[N:36]=[C:37]([N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)[S:38][C:21]=2[C:20](=[O:45])[N:19]=[C:18]1[CH2:17][N:47]1[C:48](=[O:55])[C:49]2[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]1=[O:56]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 66780417HCID 66780417, compound

Product 1

HCID 66780004HCID 66780004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.035 mL, 0.221 mmol) was added to a solution of 5-(hydroxymethyl)-4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (Example 113, 65 mg, 0.148 mmol), 1H-isoindole-1,3(2H)-dione (26.1 mg, 0.177 mmol) and triphenylphosphine (58.1 mg, 0.221 mmol) in Tetrahydrofuran (THF) (2 mL). The reaction was stirred at RT for overnight. The mixture was partitioned between DCM and NaCl solution, the organic layer was dried over MgSO4 and was concentrated. The residue was purified on a silica column eluting with 30% EtOAc/Hexanes to give the titled product, 60 mg (60%).

Workup

  1. customThe mixture was partitioned between DCM and NaCl solution
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationwas concentrated
  4. customThe residue was purified on a silica column
  5. washeluting with 30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-d33e3d934f9c40bfa922ec3c70c4470d
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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