3-Methoxyaniline → HCID 71525996, compound

HRID 1042939Notes

Reaction equation

HRID 1042939 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=O)=[CH:6][C:5]([C:19]([N:21]=[S:22]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])([CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:31])[O:29][CH3:30])=[O:23])=[O:20])=[CH:4][N:3]=1.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([NH2:48])[CH:43]=1>CN(C1C=CN=CC=1)C.ClCCCl.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:19]([N:21]=[S:22]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:29][CH3:30])=[O:31])=[O:23])=[O:20])=[CH:6][C:7]=1[C:8]#[C:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([NH:48][C:44]2[CH:45]=[CH:46][CH:47]=[C:42]([O:41][CH3:40])[CH:43]=2)=[O:15])[CH:11]=1

Participants

6

Reactant 2

HCID 108243-MethoxyanilineHCID 86668545HCID 86668545, compound

Product 1

HCID 71525996HCID 71525996, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The reaction mixture of 3-{[2-amino-5-({[bis(5-methoxy-5-oxopentyl)(oxido)-sulfanylidene]amino}carbonyl)pyridin-3-yl]ethynyl}benzoic acid (56 mg, 0.1 mmol, 1.0 equiv.), m-anisidine (13.4 μL, 0.12 mmol, 1.2 equiv.), DMAP (2.5 mg, 0.02 mmol, 0.2 equiv.) and EDC (29 mg, 0.15 mmol, 1.5 equiv.) in DCE (1 mL) in a sealed vial was stirred and heated at 60° C. for 3 hours. The resulting brown solution was diluted with EtOAc, washed with sat. aq. NaHCO3, aq. NH4Cl, and brine, and finally dried with anhydrous Na2SO4. The solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (from EtOAc-Hex 1:4 to 6:1) to yield Dimethyl 5,5′-[N-({6-amino-5-[(3-{[(3-methoxyphenyl)amino]carbonyl}phenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate

Workup

  1. washwashed with sat. aq. NaHCO3, aq. NH4Cl, and brine
  2. dry with materialfinally dried with anhydrous Na2SO4
  3. customThe solution was decanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9b92022e62104e19adb705acf38c0bfc
Source dataset
uspto-grants-2013_10
Patent number
US08558002B2

Reaction notes

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