Diisopropylethylamine → HCID 178427048, compound

HRID 2053754Notes

Reaction equation

HRID 2053754 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][CH:16]=[CH:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:49][C:50]1[CH:61]=[CH:60][C:53]2[NH:54][C:55]([CH:57]([NH2:59])[CH3:58])=[N:56][C:52]=2[CH:51]=1>O1CCCC1.O>[Cl:49][C:50]1[CH:61]=[CH:60][C:53]2[NH:54][C:55]([CH:57]([NH:59][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH:16]=[CH:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH3:58])=[N:56][C:52]=2[CH:51]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118586383-Methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 178463384HCID 178463384, compound

Product 1

HCID 178427048HCID 178427048, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.201 g (0.869 mmol) of 3-methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, 0.335 g (1.04 mmol) of TBTU and 0.33 mL (1.9 mmol) of diisopropylethylamine in 15 mL of tetrahydrofuran is stirred for 10 minutes at ambient temperature and then 0.170 g (0.869 mmol) rac.-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine are added. The mixture is stirred for 16 hours at ambient temperature, combined with water, and extracted three times with ethyl acetate. The combined organic phases are washed once with 2M NaOH and three times with water, dried with sodium sulfate, and concentrated. Yield: 0.34 g (96% of theory); Rf value: 0.50 (silica gel; dichloromethane/ethanol=9:1); C22H21ClN4O2 (408.89); mass spectrum: (M−H)−=407/409 (chlorine isotope) and (M+H)+=409/411 (chlorine isotope).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases are washed once with 2M NaOH and three times with water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dafd39c2ee3a49cbae3b46b672df498f
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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