1-Hydroxybenzotriazole → HCID 58270722, compound

HRID 222243Notes

Reaction equation

HRID 222243 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[O:9])[CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[NH2:42][CH2:43][C:44]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[F:52])=[O:45]>C(N(CC)CC)C.C(Cl)Cl>[F:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[C:44](=[O:45])[CH2:43][NH:42][C:16]([CH:13]1[CH2:12][CH2:11][N:10]([C:8]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:9])[CH2:15][CH2:14]1)=[O:18]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 132906632-Amino-1-(2-fluorophenyl)ethan-1-one--hydrogen chloride (1/1)HCID 574218421-[(Pyridin-3-yloxy)carbonyl]piperidine-4-carboxylic acid

Product 1

HCID 58270722HCID 58270722, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1-[(pyridin-3-yloxy)carbonyl]piperidine-4-carboxylic acid (500 mg) and DCM (10 mL) were added HOBt (297 mg) and WSC hydrochloride (498 mg), followed by stirring at room temperature for 30 minutes. Then, 2-amino-1-(2-fluorophenyl)ethanone hydrochloride (417 mg) and triethylamine (0.31 mL) were added thereto, followed by stirring at room temperature overnight. The reaction liquid was purified directly by silica gel column chromatography (chloroform/methanol=99/1 to 95/5) to obtain pyridin-3-yl 4-{[2-(2-fluorophenyl)-2-oxoethyl]carbamoyl}piperidine-1-carboxylate (423 mg) as a colorless solid.

Workup

  1. stirringby stirring at room temperature overnight
  2. customThe reaction liquid
  3. customwas purified directly by silica gel column chromatography (chloroform/methanol=99/1 to 95/5)

Sources & evidence

ORD record
ord-9bab9265be30469b8efb3267a0c812dd
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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