Benzoic Acid → HCID 24758044, compound

HRID 1016094Notes

Reaction equation

HRID 1016094 reaction equation
Cl.[NH2:2][C@H:3]([CH:19]([CH3:21])[CH3:20])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:41](O)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CO.C(Cl)CCl.CN(C=O)C>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH:9]2[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C@H:3]([NH:2][C:41](=[O:48])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:19]([CH3:21])[CH3:20])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67299489HCID 67299489, compound

Product 1

HCID 24758044HCID 24758044, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

(R)-2-Amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride (41 mg) was added to DMF (1 mL). The resulting mixture was stirred until homogeneous and then HOBt (19 mg), DIEA (65 μL), benzoic acid (17 mg) and EDC (26 mg) were added. The resulting solution was allowed to stir overnight at rt. After this time, the solution was diluted with MeOH and purified by preparative LC-MS to provide Example 75. MS found: (M+Na)+=421.

Workup

  1. additionwere added
  2. custompurified by preparative LC-MS
  3. customto provide Example 75

Sources & evidence

ORD record
ord-5059b660a667440abc22c5392e340df6
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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