Hydrochloric Acid → HCID 178489613, compound

HRID 1066516

Reaction equation

HRID 1066516 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:18])=[O:17])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:11]([O:35][CH3:36])[N:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].C(N(C(C)C)C(C)C)C.Cl.[NH2:47][OH:48].Cl>O1CCOCC1>[OH:48][NH:47][C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([O:35][CH3:36])[C:12]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)(=[O:17])=[O:18])[N:14]=2)[CH:6]=[CH:5][N:4]=1)=[NH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 99358945-Methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Product 1

HCID 178489613HCID 178489613, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 100 mg of 5-methyl-pyridine-2-sulfonic acid [2-(2-cyano-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide, product of example 19, in dioxane (10 ml) was treated at RT with 0.17 ml of N-etyldiisopropylamine then with 69 mg of hydroxylamine hydrochloride and refluxed 12 h until the reaction was complete according to TLC analysis. The mixture was poured into cold diluted HCl and the product extracted into AcOEt. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The solid residue was crystallised from CH2Cl2/Et2O to afford N-hydroxy-4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxamidine as off-white crystals. ISN mass spectrum, m/e 536.2 (M−1 calculated for C24H23N7O6S: 536).

Workup

  1. extractionthe product extracted into AcOEt
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe solid residue was crystallised from CH2Cl2/Et2O

Sources & evidence

ORD record
ord-663f316a461242a7a2b3528fec8d8a2e
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Linked notes

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