1,2-Dichloroethane → HCID 58914790, compound

HRID 1297504Notes

Reaction equation

HRID 1297504 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.[NH2:32][C:33]1[N:38]=[C:37]([NH:39][CH2:40][CH2:41][CH2:42][N:43]2[CH:47]=[C:46]([C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][C:49]=3[Cl:55])[CH:45]=[C:44]2[C:56](O)=[O:57])[CH:36]=[CH:35][C:34]=1[N+:59]([O-:61])=[O:60]>CN(C=O)C>[NH2:32][C:33]1[N:38]=[C:37]([NH:39][CH2:40][CH2:41][CH2:42][N:43]2[CH:47]=[C:46]([C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][C:49]=3[Cl:55])[CH:45]=[C:44]2[C:56]([NH:24][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:57])[CH:36]=[CH:35][C:34]=1[N+:59]([O-:61])=[O:60]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 13441-PyrrolidineethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68434681HCID 68434681, compound

Product 1

HCID 58914790HCID 58914790, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hünig's Base (2.5 eq), HOBT (1.2 eq), EDC (1.2 eq) and 1-(2-aminoethyl)pyrrolidine (1.5 eq) were added sequentially to a solution of 1-{3-[(6-amino-5-nitro(2-pyridyl))amino]propyl}-4-(2,4-dichlorophenyl)pyrrole-2-carboxylic acid (11) (1 eq) in DMF (2M) at room temperature with stirring. After 12 hours, the DMF was removed under high vacuum via a centrifugal evaporator. The residue is dissolved in EtOAc and washed with sat. aq. NaHCO3, dried (Na2SO4), filtered, and concentrated. The crude product was purified using a plug of silica eluting with 4% MeOH in CH2Cl2 to give (1-{3-[(6-amino-5-nitro(2-pyridyl))amino]propyl}-4-(2,4-dichlorophenyl)pyrrol-2-yl)-N-(2-pyrrolidinylethyl)carboxamide (12) as a yellow solid (13% yield, 96% pure).

Workup

  1. customthe DMF was removed under high vacuum via a centrifugal evaporator
  2. dissolutionThe residue is dissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-2ed2980bc1544e50950ee929c8ef2d3f
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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