1,2-Dichloroethane → HCID 57888652, compound

HRID 1016098Notes

Reaction equation

HRID 1016098 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][CH:43]([CH3:45])[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][CH:43]([CH3:44])[CH3:45])[CH2:34][CH2:33]2)=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 67300055HCID 67300055, compound

Product 1

HCID 57888652HCID 57888652, 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)-4-methylpentan-1-one hydrochloride (21 mg) in DIEA (65 μL) and DMF (185 μL) was added to the reaction tube. After the reaction mixture was shaken overnight at rt., the resulting solution was diluted with MeOH and purified by preparative LC-MS to provide Example 187. MS found: (M+H)+=414.

Workup

  1. stirringAfter the reaction mixture was shaken overnight at rt
  2. custompurified by preparative LC-MS
  3. customto provide Example 187

Sources & evidence

ORD record
ord-9c282f6135fd4beab3c22b848874d394
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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