1,2-Dichloroethane → HCID 89455737, compound

HRID 1776536Notes

Reaction equation

HRID 1776536 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:16]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:28][C:29]1[CH:30]=[N+:31]([O-:54])[CH:32]=[C:33]([Cl:53])[C:34]=1[CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([F:47])[F:46])=[C:40]([O:48][CH2:49][CH:50]2[CH2:52][CH2:51]2)[CH:39]=1)O.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:16]([O:18][CH2:19][C:20]([O:22][C@H:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([F:46])[F:47])=[C:40]([O:48][CH2:49][CH:50]2[CH2:51][CH2:52]2)[CH:39]=1)[CH2:35][C:34]1[C:33]([Cl:53])=[CH:32][N+:31]([O-:54])=[CH:30][C:29]=1[Cl:28])=[O:21])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 89459942HCID 89459942, compound

Product 1

HCID 89455737HCID 89455737, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoyloxy)acetic acid (0.192 g, 0.476 mmol), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.200 g, 0.476 mmol), EDC (0.274 g, 1.428 mmol), and DMAP (0.058 g, 0.476 mmol) in DCM (20 ml) was stirred at RT for 2 hours. The mixture was washed with HCl 1N and with NaHCO3 5%; the organic layer was dried over Na2SO4, and the solvent was removed. The crude was purified by flash chromatography on silica gel cartridge (DCM:MeOH=99:1) to afford (S)-4-(2-(2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.296 g, 0.367 mmol, 77% yield, MS/ESI+ 805.0 [MH]+).

Workup

  1. washThe mixture was washed with HCl 1N and with NaHCO3 5%
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customthe solvent was removed
  4. customThe crude was purified by flash chromatography on silica gel cartridge (DCM:MeOH=99:1)

Sources & evidence

ORD record
ord-945b64b8f9984684aec07bb21c247af4
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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