Triethylamine → HCID 178518673, compound

HRID 1919746Notes

Reaction equation

HRID 1919746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][OH:20])=[NH:18])=[CH:16][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29](OCC)=[O:30]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([C:17]4[NH:18][C:29](=[O:30])[O:20][N:19]=4)=[CH:16][C:10]=3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178513236HCID 178513236, compound

Product 1

HCID 178518673HCID 178518673, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-Fluoro-phenyl)-N-hydroxy-1H-benzoimidazole-5-carboxamidine (501.9 mg, 1.86 mmol, example 3), triethylamine (645 μl, 4.63 mmol) and ethyl chloroformate (229 μl, 2.4 mmol) was dissolved in 35 ml of DMF. The mixture was heated to 80° C. for 7 hours. The mixture was evaporated. Ethyl acetate and water were added, the organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 118 mg (21%) of the desired product. MS: m/e=297.05 (M+H+).

Workup

  1. customThe mixture was evaporated
  2. additionEthyl acetate and water were added
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-5866ed2e801a41f582c9d0d6843e4718
Source dataset
uspto-grants-2012_05
Patent number
US08168665B2

Reaction notes

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