Stannous chloride dihydrate → HCID 46851983, compound

HRID 1797936Notes

Reaction equation

HRID 1797936 reaction equation
O.O.[Sn](Cl)Cl.[OH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13](=[NH:42])[C:14]2[CH:15]=[C:16]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([S:30]([C:33]4[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=4)(=[O:32])=[O:31])=[CH:26][CH:25]=3)=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:8]1>C(O)(=O)C.CO>[NH2:39][C:36]1[CH:37]=[CH:38][C:33]([S:30]([C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:21]([NH:20][C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([N:10]4[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]4)=[NH:42])[CH:15]=3)=[O:22])=[CH:29][CH:28]=2)(=[O:32])=[O:31])=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 46851822HCID 46851822, compound

Product 1

HCID 46851983HCID 46851983, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of tin(II) chloride dihydrate (3 equivalents) in concentrated acetic acid was treated with a 3 M solution of chloridric acid in methanol for 30 minutes. The resulting suspension was added portionwise to a solution of 1-(3-((4-hydroxypiperidin-1-yl) (imino)methyl)phenyl)-3-(4-(4-nitrophenyl sulfonyl)phenyl)urea (10) in acetic acid. The resulting solution was stirred 2 hours at 85° C. The reaction mixture was quenched with a 5% NaOH aqueous solution, and extracted with ethyl acetate. The title compound was obtained after preparative HPLC.

Workup

  1. customThe reaction mixture was quenched with a 5% NaOH aqueous solution
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-ee9c9c6e460a4be29e577aaa89419e0b
Source dataset
uspto-grants-2013_01
Patent number
US08343963B2

Reaction notes

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