1,2-Dichloroethane → HCID 89455515, compound

HRID 1776630Notes

Reaction equation

HRID 1776630 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:28]([O:32][C:33]([N:35]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][C:48](O)=[O:49])=[CH:42][CH:41]=1)[S:36]([CH3:39])(=[O:38])=[O:37])=[O:34])([CH3:31])([CH3:30])[CH3:29].C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[C:28]([O:32][C:33]([N:35]([C:40]1[CH:41]=[CH:42][C:43]([CH2:46][CH2:47][C:48]([O:10][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)[CH:12]=2)[CH2:8][C:7]2[C:6]([Cl:26])=[CH:5][N+:4]([O-:27])=[CH:3][C:2]=2[Cl:1])=[O:49])=[CH:44][CH:45]=1)[S:36]([CH3:39])(=[O:38])=[O:37])=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 89455321HCID 89455321, compound

Product 1

HCID 89455515HCID 89455515, compoundYield 76.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (30 mg, 0.07 mmol) and 3-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)phenyl)propanoic acid (48 mg, 0.14 mmol) were dissolved in DMF (2 ml), and DMAP (17 mg, 0.14 mmol) and EDC (40 mg, 0.21 mmol) were added. The mixture was stirred at RT overnight, then was diluted with water. The precipitate was filtered, dissolved in EtOAc and washed with HCl 1N and NaHCO3 sat. sol. The organic phase was dried over Na2SO4 and evaporated under vacuum to give 40 mg of crude product, that was used for the next step without any further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. dissolutiondissolved in EtOAc
  3. washwashed with HCl 1N and NaHCO3 sat. sol. The organic phase
  4. dry with materialwas dried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-a337fe5a98fb4813985fc2cabf435c0e
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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