1,2-Dichloroethane → HCID 57889696, compound

HRID 1016092Notes

Reaction equation

HRID 1016092 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][C@H:26]([CH2:42][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])[C@H:26]([NH:25][C:11](=[O:19])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:42][CH3:43])[CH2:34][CH2:33]2)=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 67299615HCID 67299615, compound

Product 1

HCID 57889696HCID 57889696, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A reaction vessel was charged with HOBt (8 mg), benzoic acid (7 mg) and EDC (11 mg) in DMF (0.6 mL), and the resulting solution was allowed to agitate at rt. for 15 min. After this time, a solution of (R)-2-amino-1-(4-(4-chlorophenyl)piperidin-1-yl)butan-1-one hydrochloride (14 mg) in DIEA (38 μL) and DMF (187 μL) was added. Upon completion of addition, 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 1. MS found: (M+H)+=386.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was shaken overnight at rt
  3. custompurified by preparative LC-MS
  4. customto provide Example 1

Sources & evidence

ORD record
ord-b547b101ef5348f7bf185038c0b373ce
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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