Aniline → HCID 66937310, compound

HRID 1521457Notes

Reaction equation

HRID 1521457 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-03c4d3e42de443a3b33aa40a67b96505
Source dataset
uspto-grants-2015_07
Patent number
US09073923B2

Reaction notes

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