1-Hydroxybenzotriazole → N-(1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)benzamide

HRID 1016102Notes

Reaction equation

HRID 1016102 reaction equation
[C:1]([NH:9][CH:10]([C:14]([OH:16])=O)[CH:11]([CH3:13])[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([CH:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)=[CH:40][CH:39]=1>CN(C=O)C.CO.C(Cl)CCl>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([CH:44]2[CH2:45][CH2:46][N:47]([C:14](=[O:16])[CH:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]([CH3:12])[CH3:13])[CH2:48][CH2:49]2)=[CH:40][CH:39]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2266823-Methyl-2-(phenylformamido)butanoic acidHCID 27578434-(4-chlorophenyl)piperidine Hydrochloride

Product 1

HCID 57888953N-(1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)benzamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A reaction vessel was charged with benzoyl-DL-valine (24 mg), HOBt (16 mg), DIEA (57 μL), 4-(4-chlorophenyl)piperidine hydrochloride (28 mg) and EDC (23 mg) in DMF (1.5 mL) and then agitated at rt. for 16 h. At the conclusion of this period, the resulting solution was diluted with MeOH and purified by preparative LC-MS to provide Example 208. MS found: (M+H)+=399.

Workup

  1. custompurified by preparative LC-MS
  2. customto provide Example 208

Sources & evidence

ORD record
ord-4a97497072e04d5992588a16894bf84f
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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