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

HRID 1820172Notes

Reaction equation

HRID 1820172 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-7c5cf12756f244098fdeef76afa4f225
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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