Diisopropylethylamine → 4-({5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-cyclohexanecarboxylic acid

HRID 38036

Reaction equation

HRID 38036 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.N1C2C(=NC=CC=2)N([N:20]2[C:24](/[CH:25]=[C:26]3\[C:27](=[O:36])[NH:28][C:29]4[C:34]\3=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[C:23]([CH3:37])[C:22]([C:38]([O-])=[O:39])=[C:21]2[CH3:41])N=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:36])/[C:26]/2=[CH:25]\[C:24]1[NH:20][C:21]([CH3:41])=[C:22]([C:38]([NH:1][CH:2]2[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]2)=[O:39])[C:23]=1[CH3:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1715604-Aminocyclohexanecarboxylic acidHCID 131727992(Z)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 674104754-({5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-cyclohexanecarboxylic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-cyclohexanecarboxylic acid (84 mg, 0.573 mmol) was added to a solution of A4 (200 mg, 0.478=01) and DIEA (0.125 mL, 0.717=01) in 15 mL of DMF. The mixture was stirred at r.t. LC-MS was used to determine completion of the reaction. DMF was evaporated under reduced pressure and the residue was triturated with ACN for several times to provide 4-({5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-cyclohexanecarboxylic acid (180 mg, 88.5%).

Workup

  1. customcompletion of the reaction
  2. customDMF was evaporated under reduced pressure
  3. customthe residue was triturated with ACN for several times

Sources & evidence

ORD record
ord-2a63ab2607204339b855520e98fcf2b4
Source dataset
uspto-grants-2013_09
Patent number
US08524709B2

Linked notes

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