1,1'-Thiocarbonyldiimidazole → HCID 86617519, compound

HRID 2367135Notes

Reaction equation

HRID 2367135 reaction equation
[Cl:1][C:2]1[C:3]([F:27])=[C:4]([N:8]2[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([NH2:25])[CH:19]=3)([OH:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:26])[CH:5]=[CH:6][CH:7]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[S:29]>O1CCCC1>[Cl:1][C:2]1[C:3]([F:27])=[C:4]([N:8]2[C:16]([OH:17])([C:18]3[CH:23]=[CH:22][C:21]4[NH:24][C:28](=[S:29])[NH:25][C:20]=4[CH:19]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:26])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 67045347HCID 67045347, compound

Product 1

HCID 86617519HCID 86617519, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chloro-2-fluorophenyl)-3-(3,4-diaminophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (575 mg, 1.49 mmol) in tetrahydrofuran (2.0 mL) was added 1,1′-thiocarbonyldiimidazole (400 mg, 2.25 mmol) at room temperature and stirred for 4 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford 2-(3-chloro-2-fluorophenyl)-3-hydroxy-3-(2-thioxo-2,3-dihyro-1H-benzimidazol-5-yl)-2,3-dihyro-1H-isoindol-1-one (530 mg, 84%) as an off-white powder. 1H NMR (400 MHz, d6-DMSO): 12.58 (s, 1H), 12.50 (s, 1H), 7.90 (s, 1H), 7.89 (s, 1H), 7.70-7.60 (m, 2H), 7.51 (t, 1H), 7.32 (d, 1H), 7.30 (t, 1H), 7.19 (t, 1H), 7.14 (s, 1H), 7.05 (d, 1H), 6.94 (d, 1H); MS (EI) for C21H13ClFN3O2S: 426 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-02ae421db20e4a54907802f65d9535e8
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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