Triethylamine → HCID 178427057, compound

HRID 2053771Notes

Reaction equation

HRID 2053771 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.[F:18][C:19]1[CH:30]=[CH:29][C:22]2[NH:23][C:24]([CH:26]([NH2:28])[CH3:27])=[N:25][C:21]=2[CH:20]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CS(C)=O.C(OCC)(=O)C>[F:18][C:19]1[CH:30]=[CH:29][C:22]2[NH:23][C:24]([CH:26]([NH:28][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH3:27])=[N:25][C:21]=2[CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178463394HCID 178463394, compound

Product 1

HCID 178427057HCID 178427057, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.10 g (0.43 mmol) of 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, 0.184 g (0.450 mmol) of 1-(5-fluoro-1H-benzimidazol-2-yl)ethylamine×2(CF3COOH) (prepared analogously to Methods 1a, 10b, 10c) and 0.35 mL (2.50 mmol) of triethylamine in 3 mL of dimethylsulfoxide is stirred at ambient temperature and combined with 0.193 g (0.600 mmol) of TBTU. The reaction mixture is stirred for 1 hour at ambient temperature, then diluted with ethyl acetate and washed successively with 10% aqueous citric acid, twice with 2 molar sodium hydroxide solution and with water. The organic phase is dried with sodium sulfate and concentrated. The crude product is taken up in ethyl acetate, precipitated with tert-butylmethylether, and dried. Yield: 83 mg (49% of theory); Rf value: 0.34 (silica gel; ethyl acetate/ethanol=9:1); C22H23FN4O2 (394.45); mass spectrum: (M+H)+=395

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at ambient temperature
  2. washwashed successively with 10% aqueous citric acid, twice with 2 molar sodium hydroxide solution and with water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. concentrationconcentrated
  5. customprecipitated with tert-butylmethylether
  6. customdried

Sources & evidence

ORD record
ord-1f941352097c44439857730fad537154
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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