Carbon Disulfide → HCID 25192109, compound

HRID 473600Notes

Reaction equation

HRID 473600 reaction equation
Cl.[CH3:2]N(C)CCCN=C=NCC.[C:13](=[S:15])=S.[CH2:16]([N:23]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:24][C@@H:25]([NH2:27])C)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH:35]1[CH2:40][CH2:39][CH:38]([N:41]2[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[NH:43][C:42]2=[O:50])[CH2:37][CH2:36]1>C(#N)C>[CH2:28]([N:23]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@@H:24]([CH3:2])[CH2:25][NH:27][C:13]([N:35]1[CH2:36][CH2:37][CH:38]([N:41]2[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[NH:43][C:42]2=[O:50])[CH2:39][CH2:40]1)=[S:15])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12592566HCID 12592566, compound

Product 1

HCID 25192109HCID 25192109, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a stirred solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (30 mg, 0.16 mmol) in acetonitrile (0.4 mL) cooled to −10° C. under N2 was added CS2 (94 μL, 1.57 mmol). A solution of (S)—N,N-dibenzylpropane-1,2-diamine (40 mg, 0.16 mmol) in acetonitrile (0.4 mL) was added dropwise. The reaction mixture was stirred for 3 h at room temperature and a solution of 1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (34 mg, 0.16 mmol) in acetonitrile (0.8 mL) was added. The mixture was heated at 55° C. overnight and the solvent was removed on vacuo. The crude material was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate 6/4) to afford a pale yellow solid (32 mg, 40%).

Workup

  1. temperatureThe mixture was heated at 55° C. overnight
  2. customthe solvent was removed on vacuo
  3. customThe crude material was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate 6/4)

Sources & evidence

ORD record
ord-1388b01d822440c8acbf0352897d54a3
Source dataset
uspto-grants-2014_01
Patent number
US08637496B2

Reaction notes

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