1,2-Dichloroethane → HCID 57889591, compound

HRID 1016097Notes

Reaction equation

HRID 1016097 reaction equation
C1C=CC2N(O)N=NC=2C=1.[C:11]([OH:19])(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)CCl.Cl.[NH2:25][CH:26]([CH2:42][CH2:43][CH3:44])[C:27]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28]>CN(C=O)C.CCN(C(C)C)C(C)C.CO>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([CH:32]2[CH2:31][CH2:30][N:29]([C:27](=[O:28])[CH:26]([NH:25][C:11](=[O:19])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:42][CH2:43][CH3:44])[CH2:34][CH2:33]2)=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 67299486HCID 67299486, compound

Product 1

HCID 57889591HCID 57889591, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A reaction tube was charged with HOBt (13 mg), benzoic acid (9 mg) and EDC (18 mg) in DMF (0.75 mL) and then agitated at rt. for 15 min. A solution of 2-amino-1-(4-(4-chlorophenyl)piperidin-1-yl)pentan-1-one hydrochloride (20 mg) in DIEA (65 μL) and DMF (185 μL) was added to the reaction tube, and the resulting mixture was shaken overnight at rt. After this time, the resulting solution was diluted with MeOH and purified by preparative LC-MS to provide Example 180. MS found: (M+H)+=400.

Workup

  1. stirringthe resulting mixture was shaken overnight at rt
  2. custompurified by preparative LC-MS
  3. customto provide Example 180

Sources & evidence

ORD record
ord-3296af681a25426fbfd1e8b723331d70
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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