Citric Acid → HCID 178458429, compound

HRID 2236747Notes

Reaction equation

HRID 2236747 reaction equation
I[CH2:2][C:3]([OH:5])=[O:4].CN1CCOCC1.C(OC([Cl:20])=O)C(C)C.O[C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][CH2:46][CH3:47])[CH2:25][NH:26]/[CH:27]=[C:28]1\[C:29](=[O:40])[NH:30][C:31](=[O:39])[C:32]2[C:37]\1=[CH:36][C:35]([I:38])=[CH:34][CH:33]=2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Cl:20][CH2:2][C:3]([O:5][C:22]1[CH:23]=[C:24]([CH2:25][NH:26]/[CH:27]=[C:28]2\[C:29](=[O:40])[NH:30][C:31](=[O:39])[C:32]3[C:37]\2=[CH:36][C:35]([I:38])=[CH:34][CH:33]=3)[CH:41]=[CH:42][C:43]=1[O:44][CH2:45][CH2:46][CH3:47])=[O:4]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 5240Iodoacetic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178458427HCID 178458427, compound

Product 1

HCID 178458429HCID 178458429, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To iodoacetic acid (242 mg, 1.3 mmol) in N,N-dimethylformamide (2 mL) at −20 C is added N-methylmorpholine (142 uL, 1.3 mmol) and isobutylchloroformate (178 uL, 1.3 mmol). After 5 min (4Z)-4-{[(3-hydroxy-4-propoxybenzyl)amino]methylene}-6-iodoisoquinoline-1,3(2H,4H)-dione (250 mg, 0.52 mmol) is added. The reaction mixture is allowed to warm to 25 C. After 24 h 15% aq. Citric acid is added. The resulting precipitate is filtered and washed with water to give a brown solid (352 mg). A portion of this material (50 mg) is chromatographed on silica gel (CH2Cl2/MeOH) to give the title compound as a tan powder (23 mg). MS (ESI) m/z 555 (M+H)+1.

Workup

  1. temperatureto warm to 25 C
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-2125157b385f4354aba1dc94887a7f58
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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