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Triethylamine → (z)-n-(2-Amino-4-fluorophenyl)-6-(4-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)butylamino)nicotinamide

HRID 1695046
Notes
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Reaction equation

HRID 1695046 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]([OH:21])=O)[C:14]=1[CH3:22].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[NH2:52][C:53]1[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=1[NH:60][C:61](=[O:74])[C:62]1[CH:67]=[CH:66][C:65]([NH:68][CH2:69][CH2:70][CH2:71][CH2:72][NH2:73])=[N:64][CH:63]=1>[Cl-].[Na+].O.CN(C=O)C>[NH2:52][C:53]1[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=1[NH:60][C:61](=[O:74])[C:62]1[CH:67]=[CH:66][C:65]([NH:68][CH2:69][CH2:70][CH2:71][CH2:72][NH:73][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:21])=[N:64][CH:63]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10979489Sunitinib acidHCID 57993725N-(2-amino-4-fluorophenyl)-6-(4-aminobutylamino)nicotinamideHCID 178418300HCID 178418300, compound

Product 1

HCID 53355159
(z)-n-(2-Amino-4-fluorophenyl)-6-(4-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)butylamino)nicotinamide
Yield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (300 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-amino-4-fluorophenyl)-6-(4-aminobutylamino)nicotinamide (333 mg, 1.05 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (485 mg, 81%) as a yellow solid.

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8f47e1f2fc184665b0c1ee1577c65a9d
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158656B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes