1-Hydroxybenzotriazole → HCID 57917670, compound

HRID 1878411Notes

Reaction equation

HRID 1878411 reaction equation
[C:1]1([NH:7][C:8](=[O:21])[NH:9][C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[N:36]1([CH2:42][C:43]2[CH:44]=[C:45]([CH:50]=[CH:51][CH:52]=2)[C:46]([O:48][CH3:49])=[O:47])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(N(C(C)C)C(C)C)C.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:1]1([NH:7][C:8](=[O:21])[NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:39]3[CH2:38][CH2:37][N:36]([CH2:42][C:43]4[CH:44]=[C:45]([CH:50]=[CH:51][CH:52]=4)[C:46]([O:48][CH3:49])=[O:47])[CH2:41][CH2:40]3)=[O:16])=[CH:19][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2768344ethyl 4-(3-phenylureido)benzoateHCID 86635135HCID 86635135, compound

Product 1

HCID 57917670HCID 57917670, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-(3-phenylureido)benzoate (1.00 g, 3.90 mmol) in N,N-dimethylform-amide (20 mL) was added methyl 3-(piperazin-1-ylmethyl)benzoate bis(2,2,2-trifluoroacetate) (1.25 g, 2.70 mmol), N-ethyl-N-isopropylpropan-2-amine (0.94 mL, 5.40 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (0.40 g, 2.97 mmol, HOBT) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.57 g, 2,97 mmol, EDCl). The mixture was stirred overnight at room temperature and then concentrated under vacuum. The residue was taken up in ethyl acetate and washed with water (×2) and then saturated aqueous sodium chloride. The organic phase was dried on magnesium sulfate, filtered, concentrated under vacuum. Silica chromatography (10-40% ethyl acetate in n-hexanes) and recrystallisation from methanol gave the title compound (1.02 g).

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with water (×2)
  3. customThe organic phase was dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customSilica chromatography (10-40% ethyl acetate in n-hexanes) and recrystallisation from methanol

Sources & evidence

ORD record
ord-8faaa3e0acb54b40813c45d2e35b9aac
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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