1,2-Dichloroethane → HCID 57888812, compound

HRID 1820169Notes

Reaction equation

HRID 1820169 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]([C:42]([CH3:45])([CH3:44])[CH3:43])[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)[C:42]([CH3:43])([CH3:45])[CH3:44])[CH2:34][CH2:33]2)=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 67299973HCID 67299973, compound

Product 1

HCID 57888812HCID 57888812, 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 for 15 min. After this time, a solution of 2-amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3,3-dimethylbutan-1-one hydrochloride (21 mg) in DIEA (65 μL) and DMF (185 μL) was added to the tube and the reaction mixture was shaken overnight at rt. At the conclusion of this period, the resulting solution was diluted with MeOH and purified by preparative LC-MS to provide Example 194. MS found: (M+H)+=414.

Workup

  1. stirringthe reaction mixture was shaken overnight at rt
  2. custompurified by preparative LC-MS
  3. customto provide Example 194

Sources & evidence

ORD record
ord-246513b10617491bbf0b0c93ef1d5aac
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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