Chlorosuccinimide → HCID 178429111, compound

HRID 2173913Notes

Reaction equation

HRID 2173913 reaction equation
[F:1][CH:2]([F:28])[O:3][C:4]1[C:5]([C:14]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:19]=3[N:18]=2)([OH:16])[CH3:15])=[C:6]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[NH:9][CH:8]=[CH:7]2.C1C(=O)N([Cl:36])C(=O)C1>CN(C=O)C>[Cl:36][C:7]1[C:6]2[C:10](=[C:11]([CH3:13])[CH:12]=[C:4]([O:3][CH:2]([F:1])[F:28])[C:5]=2[C:14]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:19]=3[N:18]=2)([OH:16])[CH3:15])[NH:9][CH:8]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178429112(+)-2-(1-(5-(difluoromethoxy)-7-methyl-1H-indol-4-yl)-1-hydroxyethyl)-1H-benzo[d]imidazole-5-carbonitrile

Product 1

HCID 178429111HCID 178429111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (+)-2-(1-(5-(difluoromethoxy)-7-methyl-1H-indol-4-yl)-1-hydroxyethyl)-1H-benzo[d]imidazole-5-carbonitrile (32 mg, 0.083 mmol) in DMF (0.83 mL) was added NCS (17 mg, 0.12 mmol) at 0° C., and the reaction was warmed to room temperature. After 2 hours the reaction was quenched with sat. aq. Na2S2O3 and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51-12.66 (m, 1H) 11.56 (br. s., 1H) 8.04 (m) 7.79-7.83 (m) 7.64-7.70 (m) 7.44-7.56 (m) 6.83-6.89 (m) 6.75 (s, 1H) 6.64-6.70 (m) 6.46-6.51 (m) 6.07-6.20 (m, 1H) 2.45 (s, 3H) 2.18 (s, 3H). HRMS calcd. for C20H15ClF2N4O2 (M+H)+ 417.0925. found 417.0942.

Workup

  1. customAfter 2 hours the reaction was quenched with sat. aq. Na2S2O3
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-d3a53cd750d3439ab6baf165f4d3e3dc
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…