Cyanogen Bromide → HCID 67044434, compound

HRID 2367110Notes

Reaction equation

HRID 2367110 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]2([OH:30])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([CH3:12])([CH3:11])[CH3:10].[N:31]#[C:32]Br>C(O)C>[NH2:31][C:32]1[N:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:7]2[CH:6]=[CH:5][C:4]([C:13]3([OH:30])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[N:14]3[CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 67044819HCID 67044819, compound

Product 1

HCID 67044434HCID 67044434, compoundYield 0.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-{3-amino-4-[(1,1-dimethylethyl)amino]phenyl}-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (347 mg, 0.862 mmol) and cyanogen bromide (100 mg, 0.948 mmol) in anhydrous ethanol (10 mL) was heated to reflux for 6 h, at which time it was cooled to room temperature and concentrated in vacuo. The residue was taken up in ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate and brine then dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by reverse phase HPLC to afford 3-[2-amino-1-(1,1-dimethylethyl)-1H-benzimidazol-5-yl]-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (2.7 mg). 1H NMR (400 MHz, d6-DMSO): 7.76 (d, 1H), 7.61 (d, 1H), 7.56-7.53 (m, 2H), 7.32 (br s, 1H), 7.30 (d, 1H), 7.09-7.07 (m, 5H), 6.92 (d, 1H), 4.41 (d, 1H), 4.22 (d, 1H), 1.73 (s, 9H); MS (EI) for C26H26N4O2: 427 (MH+).

Workup

  1. temperatureto reflux for 6 h, at which time it
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ba052d51d6454a8ca05ba21710fd0174
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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