1,1'-Carbonyldiimidazole → HCID 67044622, compound

HRID 2261975Notes

Reaction equation

HRID 2261975 reaction equation
[Cl:1][C:2]1[C:3]([F:27])=[C:4]([N:8]2[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([NH2:25])[CH:19]=3)([OH:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:26])[CH:5]=[CH:6][CH:7]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29]>O1CCCC1>[Cl:1][C:2]1[C:3]([F:27])=[C:4]([N:8]2[C:9](=[O:26])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2([C:18]2[CH:23]=[CH:22][C:21]3[NH:24][C:28](=[O:29])[NH:25][C:20]=3[CH:19]=2)[OH:17])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67045347HCID 67045347, compound

Product 1

HCID 67044622HCID 67044622, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chloro-2-fluorophenyl)-3-(3,4-diaminophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (100 mg, 0.26 mmol) in tetrahydrofuran (3 mL) was added 1,1′-carbonyldiimidazole (63 mg, 0.39 mmol) at room temperature. The reaction mixture was stirred for 2 h, at which time the solvent was evaporated. The residue was purified by reverse phase HPLC to afford 5-[2-(3-chloro-2-fluorophenyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-1,3-dihydro-2H-benzimidazol-2-one (34 mg). 1H NMR (400 MHz, d6-DMSO): 10.63 (s, 1H), 10.52 (s, 1H), 7.84 (d, 1H), 7.72 (d, 1H), 7.68-7.58 (m, 2H), 7.50 (dt, 1H), 7.31-7.29 (m, 2H), 7.19 (t, 1H), 6.84-6.77 (m, 3H); MS (EI) for C21H13ClFN3O3: 408 (MH−).

Workup

  1. customwas evaporated
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-22148e42056b4d99b8e34cef41fb9000
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

Loading…