Triethylamine → HCID 22632922, compound

HRID 2416825Notes

Reaction equation

HRID 2416825 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[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[N:6]=2)[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:44]([O:51][NH2:52])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(N(CC)CC)C>ClCCl>[CH2:44]([O:51][NH:52][C:11]([C:10]1[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[N:6][C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[C:8]([F:14])[CH:9]=1)=[O:13])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 22632954HCID 22632954, compound

Product 1

HCID 22632922HCID 22632922, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example I-2, the reaction of 2-cyclopropylamino-5-fluoro-6-(4-methylpiperazinyl)-3-pyridinecarboxylic acid (Example H-2, 200 mg, 0.67 mmol) and HOBT (99.5 mg, 0.74 mmol) with EDCI (154.6 mg, 0.81 mmol) in dichloromethane (10 mL) followed by adding O-benzylhydroxylamine hydrochloride (0.81 mmol) and triethylamine (0.113 mL, 0.81 mmol) gave a crude oil. Purification of the oil by flash chromatography on a silica gel column with 5% of MeOH in dichloromethane provided 160 mg of the title compound as an oil.

Workup

  1. customgave a crude oil
  2. customPurification of the oil by flash chromatography on a silica gel column with 5% of MeOH in dichloromethane

Sources & evidence

ORD record
ord-c5c7e360791643508d01052bb6767f12
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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