1,2-Dichloroethane → HCID 86679531, compound

HRID 1776575Notes

Reaction equation

HRID 1776575 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:7]=[N+:8]([O-:31])[CH:9]=[C:10]([Cl:30])[C:11]=1[CH2:12][C@@H:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[C:17]([O:25][CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH:16]=1)[OH:14].[CH:32]1([CH2:35][O:36][C:37]2[CH:49]=[CH:48][C:40]([C:41]([O:43][CH2:44][C:45](O)=[O:46])=[O:42])=[CH:39][C:38]=2[CH2:50][N:51]2[CH2:56][CH2:55][O:54][CH2:53][CH2:52]2)[CH2:34][CH2:33]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[N+:8]([O-:31])[CH:9]=[C:10]([Cl:30])[C:11]=1[CH2:12][C@H:13]([O:14][C:45](=[O:46])[CH2:44][O:43][C:41](=[O:42])[C:40]1[CH:48]=[CH:49][C:37]([O:36][CH2:35][CH:32]2[CH2:34][CH2:33]2)=[C:38]([CH2:50][N:51]2[CH2:52][CH2:53][O:54][CH2:55][CH2:56]2)[CH:39]=1)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[C:17]([O:25][CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH:16]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687HCID 71092687, compoundHCID 86679530HCID 86679530, compound

Product 1

HCID 86679531HCID 86679531, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

EDC (82 mg, 0.429 mmol) was added to a solution of compound (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (120 mg, 0.286 mmol), 2-(4-(cyclopropylmethoxy)-3-(morpholinomethyl)-benzoyloxy)acetic acid (300 mg, 0.859 mmol) and DMAP (18 mg, 0.143 mmol) in DCM (1 ml) at RT under nitrogen atmosphere. The mixture was stirred at RT overnight. The mixture was then diluted with DCM and washed with NaHCO3 sat. sol., HCl 0.1N and brine. The organic phase was dried over Na2SO4, and the solvent was evaporated. The crude was purified through Preparative HPLC to give (S)-3,5-dichloro-4-(2-(2-(4-(cyclopropylmethoxy)-3-(morpholinomethyl)-benzoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)pyridine 1-oxide (150 mg, 70% yield).

Workup

  1. washwashed with NaHCO3 sat. sol., HCl 0.1N and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe crude was purified through Preparative HPLC

Sources & evidence

ORD record
ord-b845fdcb368b4d719ab0fbea931a8f0e
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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