1-Hydroxybenzotriazole → HCID 86648658, compound

HRID 43713Notes

Reaction equation

HRID 43713 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][C:17]([F:20])([F:19])[CH3:18].[Cl:21][C:22]1[N:23]=[C:24]([C:29](O)=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>ClCCl.CC(N(C)C)=O>[Cl:21][C:22]1[N:23]=[C:24]([C:29]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]2[O:15][CH2:16][C:17]([F:20])([F:19])[CH3:18])=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 86648656tert-Butyl cis(+/-)-4-amino-3-(2,2-difluoropropoxy)piperidine-1-carboxylate

Product 1

HCID 86648658HCID 86648658, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

The same operation as in Example (106d) was performed using tert-butyl cis(±)-4-amino-3-(2,2-difluoropropoxy)piperidine-1-carboxylate obtained in Example (128d) (0.68 g, 2.3 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (85% content, 0.41 g, 2 mmol), WSC hydrochloride (0.77 g, 4 mmol), HOBt (0.41 g, 3 mmol), DMA (15 mL) and dichloromethane (15 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 2/3, 3/2, 4/1) to obtain 0.85 g of the title compound as a colorless solid (94%).

Workup

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 2/3, 3/2, 4/1)

Sources & evidence

ORD record
ord-a4d3e55b7e4a487cafff0921e3bcf842
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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