Triethylamine → HCID 54236381, compound

HRID 2270214Notes

Reaction equation

HRID 2270214 reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([C:11]([OH:13])=O)=[CH:9][C:8]([F:14])=[C:7]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:6]=2)[CH2:3][CH2:2]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl.[CH2:42]([O:49][NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.ClCCl>[CH2:42]([O:49][NH:50][C:11]([C:10]1[C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[N:6][C:7]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:8]([F:14])[CH:9]=1)=[O:13])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 22632924HCID 22632924, compound

Product 1

HCID 54236381HCID 54236381, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropylamino-5-fluoro-6-pyrrolidinyl-3-pyridinecarboxylic acid (Example G-2, 215 mg, 0.80 mmol) and 1-hydroxybenzotriazole (HOBT) (119 mg, 0.88 mmol) in chloroform (10 mL) was added 1-ethyl-3-(3′-dimethylamino-propyl)carbodiimide (EDCI) (169 mg, 0.88 mmol). After being stirred at room temperature for 30 minutes, O-benzylhydroxylamine hydrochloride (141 mg, 0.88 mmol) and triethylamine (0.122 mL, 0.88 mmol) were added. The reaction mixture was heated to reflux for 4 hours, diluted with dichloromethane, washed with water, and dried on sodium sulfate. The residue was purified by flash chromatography on a silica gel column with dichloromethane as eluent giving 155 mg of the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. washwashed with water
  4. customdried on sodium sulfate
  5. customThe residue was purified by flash chromatography on a silica gel column with dichloromethane as eluent

Sources & evidence

ORD record
ord-4e3a5e37816a4abe9586735e59e0fa99
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

Loading…