Phthalimide → HCID 57885518, compound

HRID 1819459Notes

Reaction equation

HRID 1819459 reaction equation
[N+:1]([C:4]1[C:5]([NH:23][CH2:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([N:31]3[CH2:34][CH:33](O)[CH2:32]3)[CH2:27][CH2:26]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-:3])=[O:2].[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[N+:1]([C:4]1[C:5]([NH:23][CH2:24][CH:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:32][CH:33]([N:40]4[C:36](=[O:46])[C:37]5[C:38](=[CH:42][CH:43]=[CH:44][CH:45]=5)[C:39]4=[O:41])[CH2:34]3)[CH2:27][CH2:26]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:20])([F:21])[F:22])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5462977Diethyl azodicarboxylateHCID 178526822HCID 178526822, compound

Product 1

HCID 57885518HCID 57885518, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}-cyclohexyl)azetidin-3-ol (111 mg, 0.22 mmol, see Example 7), phthalimide (50 mg, 0.33 mmol) and PPh3 (127 mg, 0.48 mmol) were combined in THF (5 mL). To this mixture was added DEAD (61 mg, 0.35 mmol) and the reaction was allowed to stir at 25° C. for 18 h. The reaction was diluted with EtOAc and poured into 10% aqueous NaHCO3. The aqueous phase was separated and extracted two more times with EtOAc. The organic layers were combined, dried (Na2SO4), decanted and concentrated. The crude was purified via flash chromatography (SiO2, 1:9:90-NH4OH:CH3OH:CH2Cl2) to afford 92 mg (67%) of 2-[1-(4-{[5-nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-azetidin-3-yl]-isoindole-1,3-dione.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted two more times with EtOAc
  3. dry with materialdried (Na2SO4)
  4. customdecanted
  5. concentrationconcentrated
  6. customThe crude was purified via flash chromatography (SiO2, 1:9:90-NH4OH:CH3OH:CH2Cl2)

Sources & evidence

ORD record
ord-fece6c2e38a0431f965819d67a5d054c
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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