1-Hydroxybenzotriazole → HCID 68935326, compound

HRID 1260981Notes

Reaction equation

HRID 1260981 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][NH:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][CH:42]([C:45](O)=[O:46])[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].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]([C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)=[CH:22][CH:23]=3)=[O:30])[CH2:14][CH2:13][N:12]([C:45]([CH:42]3[CH2:43][CH2:44][N:39]([C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])[CH2:40][CH2:41]3)=[O:46])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68935331HCID 68935331, compound

Product 1

HCID 68935326HCID 68935326, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of N-[(3R,4R)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methyl-4-morpholin-4-ylbenzamide monohydrochloride (800 mg) obtained in Example 614, step 3, 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (566 mg) and triethylamine (684 μL) in acetonitrile (5 mL) were added WSC.HCl (473 mg) and HOBt (378 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 (855 mg, 79%) as a white 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-842a5ad8cf5d44c7af44c7c4c3888784
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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