Aniline → HCID 66937310, compound

HRID 408785Notes

Reaction equation

HRID 408785 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:18]2[N:22]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[C:21]3[CH:29]=[C:30]([Cl:37])[C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:32][C:20]=3[N:19]=2)[CH:17]=1)=[O:12])[CH3:9]>N1C=CC=CC=1>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:18]2[N:22]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[C:21]3[CH:29]=[C:30]([Cl:37])[C:31]([S:33](=[O:35])(=[O:34])[NH:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:32][C:20]=3[N:19]=2)[CH:17]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 6115AnilineHCID 86651253HCID 86651253, compound

Product 1

HCID 66937310HCID 66937310, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
23 °C

Procedure

Aniline (15.8 μL, 0.173 mmol) was added to a solution of 1-[6-chloro-5-chlorosulfonyl-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (75.0 mg, 0.157 mmol) in pyridine (0.79 mL) and the reaction mixture was allowed to stir at 23° C. for 1.5 h. At this point it was partitioned between EtOAc (20 mL) and water (20 mL). The aqueous layer was further extracted with EtOAc (20 mL) and the combined organic layers were washed with brine (10 mL), dried, filtered, and concentrated. The residue was purified via FCC (5-80% EtOAc/hexanes) to yield the titled compound (36.0 mg, 43% yield). MS (ESI/CI): mass calcd. for C23H24ClN5O6S, 533.1; m/z found, 534.1 [M+H]+.

Workup

  1. customAt this point it was partitioned between EtOAc (20 mL) and water (20 mL)
  2. extractionThe aqueous layer was further extracted with EtOAc (20 mL)
  3. washthe combined organic layers were washed with brine (10 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via FCC (5-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1eb4e37c55e04237b018b01677ec994c
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

Loading…