2-Fluoro-5-methylphenyl isocyanate → HCID 118130070, compound

HRID 1778151Notes

Reaction equation

HRID 1778151 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1[N:39]=[C:40]=[O:41]>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:40]([NH:39][C:33]2[CH:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]=2[F:31])=[O:41])[CH:25]=1

Participants

5

Reactant 2

HCID 27333772-Fluoro-5-methylphenyl isocyanateHCID 118130063Methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate

Product 1

HCID 118130070HCID 118130070, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]pentanoate (85.6 mg, 0.2 mmol, 1 eq) and 2-fluoro-5-methylphenyl isocyanate (29 μL, 1.1 eq) in anhydrous DMF (2 mL) was stirred at room temperature overnight. The reaction was then diluted with EtOAc, washed sequentially with aq NH4Cl, saturated aq NaHCO3, brine, and lastly dried with sodium sulfate. The clear solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (EtOAc-Hex from 1:1 to neat EtOAc). The product containing fractions were concentrated to give the title compound as a white foam (86.2 mg).

Workup

  1. washwashed sequentially with aq NH4Cl, saturated aq NaHCO3, brine
  2. dry with materiallastly dried with sodium sulfate
  3. customThe clear solution was decanted
  4. concentrationconcentrated
  5. additionThe product containing fractions
  6. concentrationwere concentrated

Sources & evidence

ORD record
ord-7b3ca9a3481f4a5e81e2ec97775bbdb0
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

Loading…