Pyridine → HCID 86679436, compound

HRID 1776485Notes

Reaction equation

HRID 1776485 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][C@@H:8]([NH2:38])[C:9]([O:11][C@H:12]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]([F:32])[F:31])=[C:25]([O:33][CH2:34][CH:35]2[CH2:37][CH2:36]2)[CH:24]=1)[CH2:13][C:14]1[C:19]([Cl:20])=[CH:18][N+:17]([O-:21])=[CH:16][C:15]=1[Cl:22])=[O:10])(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:45][O:46][C:47]1[CH:48]=[C:49]([S:55](Cl)(=[O:57])=[O:56])[CH:50]=[CH:51][C:52]=1[O:53][CH3:54]>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][C@@H:8]([NH:38][S:55]([C:49]1[CH:50]=[CH:51][C:52]([O:53][CH3:54])=[C:47]([O:46][CH3:45])[CH:48]=1)(=[O:57])=[O:56])[C:9]([O:11][C@H:12]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH:30]([F:31])[F:32])=[C:25]([O:33][CH2:34][CH:35]2[CH2:37][CH2:36]2)[CH:24]=1)[CH2:13][C:14]1[C:15]([Cl:22])=[CH:16][N+:17]([O-:21])=[CH:18][C:19]=1[Cl:20])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 86679434HCID 86679434, compound

Product 1

HCID 86679436HCID 86679436, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-((S)-2-((R)-5-acetoxy-2-aminopentanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (205 mg, 0.354 mmol) dissolved in DCM (2.5 mL), pyridine (58 μl, 0.710 mmol) and 3,4-dimethoxybenzene-1-sulfonyl chloride (168 mg, 0.710 mmol) were added. The mixture was stirred at RT for 48 hours. The mixture was then diluted with DCM and washed with NaHCO3 sat. sol., HCl 0.1M and brine. The organic phase was dried over Na2SO4, and the solvent was evaporated, to yield 284 mg of a yellow solid which was purified by preparative reverse-phase HPLC to yield 42 mg of the title compound.

Workup

  1. washwashed with NaHCO3 sat. sol., HCl 0.1M and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-12ee3b174ec94915bea10797512b037e
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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