1,2-Dichloroethane → HCID 66571158, compound

HRID 83614

Reaction equation

HRID 83614 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:48]([NH2:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C=O)C.CCOCC.CCOC(C)=O>[CH2:48]([NH:55][C:20]([CH:17]1[CH2:18][CH2:19][N:14]([C:12]([C:8]2[N:7]([CH2:6][C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:11]=[CH:10][CH:9]=2)=[O:13])[CH2:15][CH2:16]1)=[O:22])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 683802051-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 66571158HCID 66571158, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The following was dissolved in anhydrous DMF (3 mL): 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid (115 mg, 0.332 mmol), Hunig's Base (0.174 ml, 0.995 mmol), EDC (76 mg, 0.398 mmol), HOBt (60.9 mg, 0.398 mmol), and benzylamine (0.040 ml, 0.365 mmol). This was stirred at room temperature for 1 day with 3 Å molecular sieves. At this time, a 1:1 solution of EtOAc:Et2O (20 mL) was added and the organic layer was washed with 10% aq. Na2CO3 (2×10 mL) and brine (1×10 mL). The organic solution was then dried (anhydrous MgSO4) and concentrated in vacuo. Trituration in Et2O provided 101 mg of the title compound as a fine, ruddy brown solid.

Workup

  1. washthe organic layer was washed with 10% aq. Na2CO3 (2×10 mL) and brine (1×10 mL)
  2. dry with materialThe organic solution was then dried (anhydrous MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d09c387e53d24c20a5fb537a9453b272
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

Loading…