Ethyl isocyanate → HCID 178465343, compound

HRID 2053942Notes

Reaction equation

HRID 2053942 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C:10]1[CH:30]=[CH:29][C:13]([C:14]([NH:16][C@H:17]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:21]=3[N:20]=2)[CH3:18])=[O:15])=[CH:12][C:11]=1[Cl:31])=[O:9].[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33].C(N(CC)CC)C>O1CCCC1>[Cl:31][C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][C:10]=1[C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[CH2:2][NH:1][C:35]([NH:34][CH2:32][CH3:33])=[O:36])=[O:9])[C:14]([NH:16][C@H:17]([C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:21]=2[N:20]=1)[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 178462071HCID 178462071, compound

Product 1

HCID 178465343HCID 178465343, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.3 mmol) of 4-[(2R)-2-aminomethylpyrrolidin-1-ylcarbonyl]-3-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]benzamide, 26 mg (0.36 mmol) of ethyl isocyanate, and 0.2 mL (1.2 mmol) of triethylamine are stirred for 16 hours at ambient temperature in 20 mL of tetrahydrofuran. Then the solvent is distilled off and the residue is chromatographed on silica gel, eluting with dichloromethane/ethanol (9:1). Yield: 140 mg (86%); Rf value: 0.38 (silica gel; dichloromethane/ethanol=9:1); C25H28Cl2N6O3 (531.44); mass spectrum: (M+H)+=531/533 (chlorine isotope) and (M−H)−=529/531 (chlorine isotope).

Workup

  1. distillationThen the solvent is distilled off
  2. customthe residue is chromatographed on silica gel
  3. washeluting with dichloromethane/ethanol (9:1)

Sources & evidence

ORD record
ord-89b98595341247379edca44ff71372b3
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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