Amrinone → HCID 58692572, compound

HRID 423234Notes

Reaction equation

HRID 423234 reaction equation
[CH:1]1[C:6]([C:7]2[CH:13]=[C:12]([NH2:14])[C:10](=[O:11])[NH:9][CH:8]=2)=[CH:5][CH:4]=[N:3][CH:2]=1.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[O:11]=[C:10]1[NH:9][CH:8]=[C:7]([C:6]2[CH:1]=[CH:2][N:3]=[CH:4][CH:5]=2)[CH:13]=[C:12]1[NH:14][S:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 3698AmrinoneHCID 7369Benzenesulfonyl chloride

Product 1

HCID 58692572HCID 58692572, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Amrinone (100 mg, 0.53 mmol) was suspended in pyridine (2 mL) and benzenesulfonyl chloride (75 μL, 0.59 mmol) was added dropwise at 0° C. The reaction mixture was stirred for 2 hours. The pyridine was removed in vacuo. MeOH was added to the crude mixture and the solid was filtered and rinsed with more MeOH to give the title compound as a light yellow solid (100 mg, 57% yield). MS (ES+) m/e=328. 1H NMR (DMSO-d6) δH 7.51 (2H, dd), 7.54-7.58 (2H, m), 7.61-7.65 (1H, m), 7.75 (2H, dd), 7.90 (2H, dd), 8.56 (2H, dd), 9.78 (1H, br s), 12.33 (1H, br s).

Workup

  1. customThe pyridine was removed in vacuo
  2. additionMeOH was added to the crude mixture
  3. filtrationthe solid was filtered
  4. washrinsed with more MeOH

Sources & evidence

ORD record
ord-886a4005cd8f43f8bd3333ff7f1c7dc0
Source dataset
uspto-grants-2012_01
Patent number
US08101770B2

Reaction notes

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