1,2-Dichloroethane → HCID 86679576, compound

HRID 1776617Notes

Reaction equation

HRID 1776617 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][C:15]([O:17][C@H:18]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]3[CH2:43][CH2:42]3)[CH:30]=2)[CH2:19][C:20]2[C:25]([Cl:26])=[CH:24][N+:23]([O-:27])=[CH:22][C:21]=2[Cl:28])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(O)=[O:2].[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Cl:28][C:21]1[CH:22]=[N+:23]([O-:27])[CH:24]=[C:25]([Cl:26])[C:20]=1[CH2:19][C@@H:18]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[O:17][C:15](=[O:16])[CH2:14][NH:13][S:10]([C:7]1[CH:8]=[CH:9][C:4]([C:1]([N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)=[O:2])=[CH:5][CH:6]=1)(=[O:11])=[O:12]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 86679575HCID 86679575, compound

Product 1

HCID 86679576HCID 86679576, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-4-(2-(2-(4-carboxyphenylsulfonamido)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (30 mg, 0.045 mmol), morpholine (19.76 mg, 0.227 mmol), DMAP (11.08 mg, 0.091 mmol) and EDC (43.5 mg, 0.227 mmol) were dissolved in DMF (1.5 ml). The reaction was stirred at RT overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by preparative reverse-phase HPLC to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-(morpholine-4-carbonyl)phenylsulfonamido)-acetoxy)ethyl)pyridine 1-oxide (15 mg, 0.021 mmol, 45.3% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-8ff06ca6fbc647be85b69a2adc1f1493
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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