Ethyl Acetate → 3-[4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylamino]-propan-1-ol

HRID 1047499Notes

Reaction equation

HRID 1047499 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27].C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]2[NH:23][CH2:24][CH2:25][CH2:26][OH:27])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 90863-Amino-1-propanolHCID 10340Sodium CarbonateHCID 582522424-((4-Chlorophenyl)sulfonyl)-5,8-difluoro-2H-chromene

Product 1

HCID 670069063-[4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylamino]-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2H-chromene (0.3 g, 0.88 mmole) was dissolved in 15 ml THF and 3-aminopropanol (1 ml) was added. The mixture was stirred at room temperature for 30 minutes. 50 saturated Na2CO3 solution and 50 ml EtOAc were added. The organic layer was washed with water (50 ml), brine (50 ml), dried over Na2SO4 and concentrated. The product was purified by column (EtOAc/hexane from 50/50 to 100/0 in 45 minutes). Yield: 0.31 g, 84%. 1H NMR (CDCl3 400 MHz) δ 7.69 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.1 Hz), 6.99 (td, J=9.5, 5.1 Hz, 1H), 6.38 (td, J=9.5, 3.7 HZ, 1H), 4.80 (dd, J=12.5, 2.9 Hz, 1H), 4.53 (s, 1H), 4.43 (d, J=11.8 Hz, 1H), 3.78 (s, 1H), 3.61 (t, J=5.9 Hz, 2H), 2.86-2.71 (m, 2H), 2.25 (bs, 1H), 1.57 (p, J=5.9 Hz, 2H).

Workup

  1. washThe organic layer was washed with water (50 ml), brine (50 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by column (EtOAc/hexane from 50/50 to 100/0 in 45 minutes)

Sources & evidence

ORD record
ord-ec183cace75e47768d5b15177a0d58bc
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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