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1,2-Dichloroethane → HCID 57889478, compound

HRID 1820165
Notes
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Reaction equation

HRID 1820165 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 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-32141e96c3b54a65a492aa6c19ffbd43
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601844B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes