Water → HCID 57925844, compound

HRID 509295Notes

Reaction equation

HRID 509295 reaction equation
CC(N(C1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[NH:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1)=[O:23])C(=O)[O-])(C)C.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.[K].[I-].[K+].[OH2:46].C[N:48]([CH:50]=[O:51])[CH3:49]>>[O:37]=[C:35]1[C:34]2[C:33](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:32](=[O:42])[N:36]1[CH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:22]([NH:21][C:10]2[CH:11]=[C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[CH:14][C:49]=2[NH:48][C:50](=[O:51])[O:46][C:12]([CH3:15])([CH3:13])[CH3:11])=[O:23])=[CH:29][CH:28]=1

Participants

6

Reactant 5

HCID 962WaterHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 1317332471,1-Dimethylethyl[3-({[4-(chloromethyl)phenyl]carbonyl}amino)biphenyl-4-yl]carbamate

Product 1

HCID 57925844HCID 57925844, compound

Procedure

1,1-dimethylethyl[3-({[4-(chloromethyl)phenyl]carbonyl}amino)biphenyl-4-yl]carbamate (20 g, 45.8 mmol), potassium phthalimide (9.33 g, 50.4 mmol) and potassium iodide (1.52 g, 9.15 mmol) were stirred in DMF (81 mL) at 50° C. overnight. Room temperature was attained, H2O was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated in MeOH to give 1,1-dimethylethyl {3-[({4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}carbonyl)amino]biphenyl-4-yl}carbamate as a pale yellow solid.

Workup

  1. customRoom temperature
  2. extractionthe products extracted into EtOAc (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in MeOH

Sources & evidence

ORD record
ord-4edc9a35262f42b6bcdee5b8e665d6db
Source dataset
uspto-grants-2015_08
Patent number
US09096559B2

Reaction notes

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