Chlorosuccinimide → HCID 178489080, compound

HRID 2173939Notes

Reaction equation

HRID 2173939 reaction equation
[OH:1][C:2]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:18]=2[N:17]=1)([C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH3:3].C1C(=O)N([Cl:34])C(=O)C1>CN(C=O)C>[Cl:34][C:6]1[C:5]2[C:9](=[C:10]([CH3:15])[CH:11]=[C:12]([O:13][CH3:14])[C:4]=2[C:2]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:18]=3[N:17]=2)([OH:1])[CH3:3])[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178489066HCID 178489066, compound

Product 1

HCID 178489080HCID 178489080, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (−)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (Example 26-C) (20 mg, 0.058 mmol) in DMF (0.58 mL) was added NCS (14 mg, 0.1 mmol) at 0° C. The reaction was stirred in the ice bath for 1 hour. At this point, the reaction was quenched with a saturated solution of aq. Na2S2O3 at 0° C., and then the mixture was extracted with EtOAc and then the EtOAc layer was dried, concentrated, absorbed onto silica and purified by flash column chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.18-12.43 (m, 1H) 11.29 (br. s., 1H) 8.06 (s) 7.65-7.79 (m) 7.45-7.52 (m) 7.43 (d, J=3.03 Hz, 1H) 6.72 (s, 1H) 5.78-6.09 (m, 1H) 3.16 (s, 3H) 2.42 (s, 3H) 2.15 (s, 3H). HRMS calcd. for C20H17ClN4O2 (M+H)+ 381.1113. found 381.1123.

Workup

  1. customAt this point, the reaction was quenched with a saturated solution of aq. Na2S2O3 at 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialthe EtOAc layer was dried
  4. concentrationconcentrated
  5. customabsorbed onto silica
  6. custompurified by flash column chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-4683abdf4b52469bac27d6872fbb893e
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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