HCID 58423331, compound → HCID 58423095, compound

HRID 1398013Notes

Reaction equation

HRID 1398013 reaction equation
[CH3:1][N:2]([CH3:25])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:9]=2/[CH:10]=[C:11]2/[C:12](=[O:17])[NH:13][C:14](=[O:16])[S:15]/2)[CH2:4]1>CO.Cl.O.[Fe]>[NH2:22][C:19]1[CH:20]=[CH:21][C:8]([N:5]2[CH2:6][CH2:7][CH:3]([N:2]([CH3:1])[CH3:25])[CH2:4]2)=[C:9]([CH:18]=1)/[CH:10]=[C:11]1/[C:12](=[O:17])[NH:13][C:14](=[O:16])[S:15]/1

Participants

6

Reactant 1

HCID 58423331HCID 58423331, compound

Product 1

HCID 58423095HCID 58423095, compoundYield 54.8%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 962WaterCatalystHCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (Z)-5-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-nitrobenzylidene)thiazolidine-2,4-dione (100 mg, 0.28 mmol) (Method 149) and iron (154 mg, 2.76 mmol) chip in MeOH (10 mL) was added 5 drops of conc. HCl and 5 drops of water. The mixture was stirred at 80° C. for 1 hr. The mixture was loaded into silica gel, purified with ISCO (100% ethyl acetate to methanol/ethyl acetate=50%) to yield a red solid which was repurified with Gilson (acetonitrile:water:0.1% TFA=0% to 50% fro 7 min) to yield a yellow solid as (Z)-5-(5-amino-2-(3-(dimethylamino)pyrrolidin-1-yl)benzylidene)thiazolidine-2,4-dione (51.0 mg, 38.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.55 (brs, 1 H), 11.32 (brs, 1 H), 10.30 (brs, 2 H), 7.80 (s, 1 H), 7.42 (m, 2 H), 7.19 (m, 1 H), 3.95 (m, 1 H), 3.39-3.27 (m, 4 H), 2.78 (s, 6 H), 2.30-2.10 (m, 2 H); m/z 333.

Workup

  1. custompurified with ISCO (100% ethyl acetate to methanol/ethyl acetate=50%)
  2. customto yield a red solid which
  3. customwas repurified with Gilson (acetonitrile:water:0.1% TFA=0% to 50% fro 7 min)

Sources & evidence

ORD record
ord-942af99b032147f9839e4afcd297d7ae
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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