1,2-Dichloroethane → HCID 57889973, compound

HRID 1016197Notes

Reaction equation

HRID 1016197 reaction equation
[CH3:1][CH:2]([CH3:14])[C@@H:3]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:4]([OH:6])=O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@:22]2([OH:30])[CH2:27][CH2:26][NH:25][CH2:24][C:23]2([CH3:29])[CH3:28])=[CH:18][CH:17]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@:22]2([OH:30])[CH2:27][CH2:26][N:25]([C:4](=[O:6])[C@H:3]([NH:7][C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)[CH:2]([CH3:1])[CH3:14])[CH2:24][C:23]2([CH3:28])[CH3:29])=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-olHCID 57889332HCID 57889332, compound

Product 1

HCID 57889973HCID 57889973, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-3-Methyl-2-(pyridine-3-ylamino)butanoic acid (162 mg, 0.83 mmol), (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (200 mg, 0.83 mmol), EDC (320 mg, 1.67 mmol), HOBT (113 mg, 0.83 mmol), DIPEA (431 mg, 3.34 mmol), and DMF (4 mL) was stirred overnight at rt. Example 607 was isolated as a greenish solid using preparative reverse phase HPLC (22.5 mg, 6.5% yield). M+H=416.18.

Workup

  1. customExample 607 was isolated as a greenish solid

Sources & evidence

ORD record
ord-de3f74e18e144e55997f203afcd8f56a
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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