1,2-Dichloroethane → HCID 86681681, compound

HRID 571265Notes

Reaction equation

HRID 571265 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].C(Cl)CCl.[F:32][C:33]1[CH:41]=[C:40]2[C:36]([C:37](=[O:47])[C:38](=[O:46])[N:39]2[CH2:42][C:43](O)=[O:44])=[CH:35][CH:34]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[O:10][C:43](=[O:44])[CH2:42][N:39]1[C:40]2[C:36](=[CH:35][CH:34]=[C:33]([F:32])[CH:41]=2)[C:37](=[O:47])[C:38]1=[O:46]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 16774742HCID 16774742, compoundHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86681681HCID 86681681, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.200 g, 0.476 mmol) in DCM (15 ml), DMAP (0.058. g, 0.476 mmol), EDC (0.274 g, 1.428 mmol) and 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetic acid (0.127 g, 0.571 mmol) were added in one portion at room temperature. The resulting solution was stirred at room temperature for 24 hours; the solvent was removed under vacuum and the residue was dissolved in ethyl acetate (40 ml), washed with a saturated solution of NaHCO3 (20 ml), with 1N HCl (20 ml) and finally with brine (20 ml). The organic layer was dried over sodium sulfate and the solvent was evaporated under vacuum. The crude was purified by preparative HPLC (Method 1) and two pure fractions were isolated:

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (40 ml)
  3. washwashed with a saturated solution of NaHCO3 (20 ml), with 1N HCl (20 ml) and finally with brine (20 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customThe crude was purified by preparative HPLC (Method 1) and two pure fractions
  7. customwere isolated

Sources & evidence

ORD record
ord-9e97667179ee492a9a5465eccd10a121
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…