2-Methyl-2-thiopseudourea sulfate → HCID 140517263, compound

HRID 2193488Notes

Reaction equation

HRID 2193488 reaction equation
[C:1]([O:4][CH:5]1[CH2:18][CH2:17][CH:16]2[CH:7]([C:8]3[C:13]([C:14]([C:19]4[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=4)=[N:15]2)=[CH:12][C:11]([O:28][CH3:29])=[C:10]([O:30][CH3:31])[CH:9]=3)[CH2:6]1)(=[O:3])[CH3:2].[CH3:32][S:33][C:34]([NH2:36])=[NH:35].OS(O)(=O)=O.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)C(C)C)C>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:29][O:28][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:30][CH3:31])[CH:7]1[CH:16]([CH2:17][CH2:18][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6]1)[N:15]=[C:14]2[C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:36][C:34](=[NH:35])[S:33][CH3:32])=[O:25])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68655284HCID 68655284, compound2×

Product 1

HCID 140517263HCID 140517263, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

3.051 g of 4-((2RS,4aRS,10bRS)-2-acetoxy-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-6-yl)-benzoic acid (compound B1), 3.00 g of S-methylisothiourea-sulfate and 10 mg of 4-dimethylaminopyridine are dissolved in 50 ml of acteonitril, than 1.80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1, 23 ml of N-ethyl-diisopropylamin are added. After stirring for 16 hours the solvent is removed. The residue is dissolved in 20 ml of water and extracted with dichloromethane. After drying the combined organic layers with magnesium sulfate the solvent is removed to yield 3.652 g of the title compound as a yellow foam which is directly submitted to further reaction without purification.

Workup

  1. additionare added
  2. customis removed
  3. dissolutionThe residue is dissolved in 20 ml of water
  4. extractionextracted with dichloromethane
  5. dry with materialAfter drying the combined organic layers with magnesium sulfate the solvent
  6. customis removed

Sources & evidence

ORD record
ord-337af583a6e9418c8d88af497f16ec9d
Source dataset
uspto-grants-2012_12
Patent number
US08329906B2

Reaction notes

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