Diisopropylethylamine → benzyl N-[2-[(3-chloropyrazine-2-carbonyl)amino]-2-iminoethyl]carbamate

HRID 2076833Notes

Reaction equation

HRID 2076833 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:42]([O:49][C:50](=[O:56])[NH:51][CH2:52][C:53](=[NH:55])[NH2:54])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.ClCCl>[CH2:42]([O:49][C:50](=[O:56])[NH:51][CH2:52][C:53]([NH:55][C:8]([C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)=[O:10])=[NH:54])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 244144Benzyl 2-amino-2-iminoethylcarbamateHCID 15019003-Chloro-2-pyrazine-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 140529508benzyl N-[2-[(3-chloropyrazine-2-carbonyl)amino]-2-iminoethyl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen, 3-chloro-2-pyrazinecarboxylic acid (76 mg), TBTU (168 mg), and diisopropylethylamine (310 mg) were added to a solution of carbamimidoylmethyl-carbamic acid benzyl ester [77390-81-9] (99 mg) in DMF (6 ml). The reaction mixture was stirred for 2 h at ambient temperature, diluted with dichloromethane and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. The obtained, crude title compound (220 mg) was used without further purification in the next step.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe obtained, crude title compound (220 mg) was used without further purification in the next step

Sources & evidence

ORD record
ord-c59ee54533064021b929864651a17e2e
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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