Hydrochloric Acid → HCID 131723910, compound

HRID 1827110Notes

Reaction equation

HRID 1827110 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:17][C:16]([CH3:18])=[C:15]([C:19](O)=[O:20])[C:14]=1[CH3:22].Cl.O[N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33]C=2N=N1.[NH2:34][CH2:35][CH2:36]C1C=CC=CN=1>CN(C=O)C.C([O-])(O)=O.[Na+].O.C(Cl)CCl>[N:25]1([CH2:36][CH2:35][NH:34][C:19]([C:15]2[C:14]([CH3:22])=[C:13](/[CH:12]=[C:5]3\[C:6](=[O:11])[NH:7][C:8]4[C:4]\3=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)[NH:17][C:16]=2[CH3:18])=[O:20])[CH:29]=[CH:30][CH:31]=[CH:32][CH2:33]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 759192-PyridineethanamineHCID 10979489Sunitinib acid

Product 1

HCID 131723910HCID 131723910, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (120 mg, 0.4 mmol) was shaken with EDC, HCl (96 mg, 0.5 mmol), anhydrous 1-hydroxy-benztriazole (68 mg, 0.5 mmol), and 2-(2-aminoethylpyridine purchased from Aldrich in anhydrous DMF (3 mL) for 2–3 days at room temperature. The reaction mixture was diluted with 1M NaHCO3 (1.5 ml), then with 8 ml of water. The precipitated crude product was collected by filtration, washed with water, dried and purified by crystallization or chromatography to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [2-(pyridin-1-yl)-ethyl]amide.

Workup

  1. customThe precipitated crude product
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried
  5. custompurified by crystallization or chromatography

Sources & evidence

ORD record
ord-b48bb249ee9b465f938c42674ccc18e7
Source dataset
uspto-grants-2006_05
Patent number
US07053114B2

Reaction notes

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