Ethanol → HCID 178465760, compound

HRID 2367087Notes

Reaction equation

HRID 2367087 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:26])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:27][O:28][C:29]([NH:31][C:32](=NC(OC)=O)SC)=[O:30].[CH2:40](O)[CH3:41]>>[CH3:27][O:28][C:29](=[O:30])[NH:31][C:32]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3([O:26][CH2:40][CH3:41])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:18])[N:10]3[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 67044654HCID 67044654, compound

Product 1

HCID 178465760HCID 178465760, compound

Procedure

A solution of 3-(3,4-diaminophenyl)-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (1.5 g, 4.34 mmol) and 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (1.8 g, 8.68 mmol) in anhydrous ethanol (15 mL) was heated to 95° C. and stirred for 18 h, at which time the reaction mixture was cooled to room temperature. The white precipitate was filtered and the powder was triturated in hot ethanol (50 mL). The white powder was collected by filtration to afford methyl{5-[1-(ethyloxy)-3-oxo-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-yl]-1H-benzimidazol-2-yl}carbamate (700 mg). 1H NMR (400 MHz, d6-DMSO): 7.82-7.81 (m, 1H), 7.58-7.52 (m, 3H), 7.51 (d, 1H), 7.33-7.16 (m, 6H), 6.90 (d, 1H), 4.75 (d, 1H), 4.75 (d, 1H), 3.79 (d, 1H), 2.74-2.67 (m, 2H), 0.65 (t, 3H); 13C NMR (100 MHz, d6-DMSO): 166.9, 154.5, 147.8, 145.7, 137.6, 132.6, 131.1, 130.7, 130.6, 129.4, 128.3, 127.8, 126.8, 122.9, 122.8, 118.9, 95.3, 57.9, 52.4, 42.5, 14.1; MS (EI) for C26H24N4O4: 457 (MH+).

Workup

  1. filtrationThe white precipitate was filtered
  2. customthe powder was triturated in hot ethanol (50 mL)
  3. filtrationThe white powder was collected by filtration

Sources & evidence

ORD record
ord-9fc4559f6f2e43e19a1df01acf139b50
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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