Diisopropylethylamine → HCID 178500555, compound

HRID 1823764Notes

Reaction equation

HRID 1823764 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH2:5][C:6]([NH2:8])=[O:7].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[N:43]1([C:48]2[CH:53]=[CH:52][C:51]([S:54]([O:57][C:58]3[CH:67]=[CH:66][C:61]4[NH:62][C:63](N)=[N:64][C:60]=4[CH:59]=3)(=[O:56])=[O:55])=[CH:50][CH:49]=2)[CH:47]=[CH:46][N:45]=[CH:44]1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH2:5][C:6]([NH:8][C:63]1[NH:62][C:61]2[CH:66]=[CH:67][C:58]([O:57][S:54]([C:51]3[CH:52]=[CH:53][C:48]([N:43]4[CH:47]=[CH:46][N:45]=[CH:44]4)=[CH:49][CH:50]=3)(=[O:56])=[O:55])=[CH:59][C:60]=2[N:64]=1)=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12550576Methyl 3-carbamoylpropanoateHCID 178508206HCID 178508206, compound

Product 1

HCID 178500555HCID 178500555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

8.9 mg of succinamic acid methyl ester, 25 mg of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) and 12 μl diisopropyl-ethylamine were taken up in 0.4 ml dimethylformamide. Reaction mixture was stirred at room temperature for one hour and 5-(4-[1-imidazolyl]-phenylsulfonyloxy)-1H-benzimidazole-2-ylamine was added in 0.2 ml dimethylformamide. Reaction mixture was then stirred at room temperature for 24 hours. Solvent was evaporated in a Jouan model RC 10.10 centrifuge evaporator and title compound was solubilised in 0.5 ml dimethylsulfoxide for LCMS trigged purification yielding 3.9 mg of N-[5-(4-[1-imidazolyl]-phenylsulfonyloxy)-1H-benzimidazole-2-yl]-succinamic-acid-methyl ester. (LC/MS analysis: retention time=2.70 min., mass spectrum: 470.34, [M+H]+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. stirringwas then stirred at room temperature for 24 hours
  4. customSolvent was evaporated in a Jouan model RC 10.10 centrifuge evaporator and title compound
  5. custompurification

Sources & evidence

ORD record
ord-ddd8504d542740eaa916fe4b1ce00606
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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