Triethylamine → HCID 178427187, compound

HRID 2053899Notes

Reaction equation

HRID 2053899 reaction equation
[NH2:1][CH2:2][CH2:3][C@H:4]([NH:15][C:16](=[O:31])[C:17]1[CH:22]=[CH:21][C:20]([C:23]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[C:19]([CH3:30])[CH:18]=1)[C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:7]=2[N:6]=1.C(N(CC)CC)C.[Cl:39][CH2:40][CH2:41][N:42]=[C:43]=[O:44]>O1CCCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:8]2[NH:9][C:5]([C@@H:4]([NH:15][C:16](=[O:31])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])=[C:19]([CH3:30])[CH:18]=3)[CH2:3][CH2:2][NH:1][C:43]([NH:42][CH2:41][CH2:40][Cl:39])=[O:44])=[N:6][C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 178427186HCID 178427186, compound

Product 1

HCID 178427187HCID 178427187, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.3 g (0.528 mmol) of (1S)—N-[3-amino-1-(5-chloro-1H-benzimidazol-2-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is suspended in 10 mL of tetrahydrofuran and 0.1 mL (1.056 mmol) of triethylamine and, after the addition of 56 mg (0.528 mmol) of 2-chloroethyl isocyanate, stirred for 16 hours at ambient temperature. Then the solution is concentrated, the residue is taken up in dichloromethane, washed several times with water, and the combined organic extracts are dried and concentrated by evaporation. Yield: 49%; Rf value: 0.30 (silica gel; dichloromethane/ethanol=9:1); C26H30Cl2N6O3 (545.47); mass spectrum: (M+H)+=545/547 (chlorine isotope).

Workup

  1. concentrationThen the solution is concentrated
  2. washwashed several times with water
  3. customthe combined organic extracts are dried
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b2f456a8982d4037bf1efc57db599d43
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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