1,1'-Carbonyldiimidazole → HCID 117600921, compound

HRID 1773662Notes

Reaction equation

HRID 1773662 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:9]2[C:10]([CH3:15])=[N:11][O:12][C:13]=2[CH3:14])=[CH:4][C:3]=1[S:16]([NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)(=[O:18])=[O:17].C1N=CN([C:30](N2C=NC=C2)=[O:31])C=1>CN(C=O)C>[CH:20]1([NH:19][S:16]([C:3]2[C:2]3[NH:1][C:30](=[O:31])[NH:8][C:7]=3[CH:6]=[C:5]([C:9]3[C:10]([CH3:15])=[N:11][O:12][C:13]=3[CH3:14])[CH:4]=2)(=[O:17])=[O:18])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 117601370HCID 117601370, compound

Product 1

HCID 117600921HCID 117600921, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2,3-Diamino-N-cyclopentyl-5-(3,5-dimethylisoxazol-4-yl)benzenesulfonamide (58 mg, 0.17 mmol) was dissolved in DMF (2 mL). To the solution was added CDI (360 mg, 4 mmol) and TEA (1 mL). The reaction was heated at 150° C. in microwave for 10 h. The solvent was evaporated and the residue was purified by preparative HPLC (0-100% CH3CN/H2O) to afford N-cyclopentyl-6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-sulfonamide.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (0-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-8f8a4ea500ec4d5d92c1e90ef61d354a
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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