1,2-Dichloroethane → HCID 86679501, compound

HRID 1776545Notes

Reaction equation

HRID 1776545 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].[NH2:28][C:29](=[O:51])[CH2:30][N:31]([C:36]1[CH:37]=[C:38]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[C:39]([O:41][CH2:42][C:43](O)=[O:44])=[O:40])[S:32]([CH3:35])(=[O:34])=[O:33].C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[NH2:28][C:29](=[O:51])[CH2:30][N:31]([C:36]1[CH:37]=[C:38]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[C:39]([O:41][CH2:42][C:43]([O:10][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)[CH2:8][C:7]1[C:6]([Cl:26])=[CH:5][N+:4]([O-:27])=[CH:3][C:2]=1[Cl:1])=[O:44])=[O:40])[S:32]([CH3:35])(=[O:34])=[O:33]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687HCID 71092687, compoundHCID 86679500HCID 86679500, compound

Product 1

HCID 86679501HCID 86679501, compoundYield 36.7%

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, 0.071 mmol), 2-(3-(N-(2-amino-2-oxoethyl)methylsulfonamido)-4-methoxybenzoyloxy)acetic acid (51.4 mg, 0.143 mmol), DMAP (15 mg, 0.123 mmol), and EDC (100 mg, 0.522 mmol) were dissolved in DMF (2 ml). The reaction was stirred at RT for 3 hours to achieve completion. The reaction mixture was diluted with Water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum. The crude product was crystallized in EtOH to give (S)-4-(2-(2-(3-(N-(2-amino-2-oxoethyl)methylsulfonamido)-4-methoxybenzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (20 mg, 0.026 mmol, 36.7% yield).

Workup

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was crystallized in EtOH

Sources & evidence

ORD record
ord-dfa92840cfb044878fbe3657016bbf3d
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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