1,2-Dichloroethane → HCID 57889478, compound

HRID 1016095Notes

Reaction equation

HRID 1016095 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]([CH:42]([CH3:45])[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])[C@H:26]([NH:25][C:11](=[O:19])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:42]([CH3:45])[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 67299541HCID 67299541, compound

Product 1

HCID 57889478HCID 57889478, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A reaction tube was charged with HOBt (8 mg), benzoic acid (7 mg) and EDC (11 mg) in DMF (0.6 mL) and then agitated at rt. for 15 min. After this time, a solution of (2R)-2-amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylpentan-1-one hydrochloride (16 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 150. MS found: (M+H)+=414.

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 150

Sources & evidence

ORD record
ord-223e00586991412cb9723951c5caa66d
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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