1-Hydroxybenzotriazole → HCID 68932418, compound

HRID 1260983Notes

Reaction equation

HRID 1260983 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C@H:15]([N:16]([CH3:31])[C:17](=[O:30])[C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)[CH2:14][CH2:13][N:12]([C:32]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[O:33])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[OH:40][C:41]1([C:44](O)=[O:45])[CH2:43][CH2:42]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(#N)C.O.C(N(CC)CC)C>[Cl:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C@H:15]([N:16]([CH3:31])[C:17](=[O:30])[C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:22][CH:23]=3)[CH2:14][CH2:13][N:12]([C:32]([CH:34]3[CH2:39][CH2:38][N:37]([C:44]([C:41]4([OH:40])[CH2:43][CH2:42]4)=[O:45])[CH2:36][CH2:35]3)=[O:33])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acidHCID 68932408HCID 68932408, compound

Product 1

HCID 68932418HCID 68932418, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylcarbonyl)piperidin-4-yl]-N-methyl-4-morpholin-4-ylbenzamide monohydrochloride (200 mg) obtained in Example 621, 1-hydroxycyclopropanecarboxylic acid (44.5 mg) and triethylamine (143 μL) in acetonitrile (5 mL) were added WSC.HCl (96 mg) and HOBt (76.8 mg), and the mixture was stirred at room temperature for 14 hr. To the reaction solution was added water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (119 mg, 55%) as a white crystal powder.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40f8a5589ad24194a05f5ad627532591
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

Loading…