p-Toluenesulfonic acid monohydrate → HCID 86717561, compound

HRID 712110Notes

Reaction equation

HRID 712110 reaction equation
[NH2:1][C:2]1[C:3]([NH:11][C:12]2([CH2:22][OH:23])[CH2:21][CH2:20][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH2:13]2)=[C:4]2[S:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[CH:24]([O-])([O-])OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:11]1([C:12]2([CH2:22][OH:23])[CH2:21][CH2:20][C:15]3([O:16][CH2:17][CH2:18][O:19]3)[CH2:14][CH2:13]2)[C:3]2=[C:4]3[S:10][CH:9]=[CH:8][C:5]3=[N:6][CH:7]=[C:2]2[N:1]=[CH:24]1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53630039EthylorthoformateHCID 86717562HCID 86717562, compound

Product 1

HCID 86717561HCID 86717561, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of {8-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]-1,4-dioxaspiro[4.5]dec-8-yl}methanol (90.0 mg, 0.268 mmol), ethyl orthoformate (112 μL, 0.671 mmol), and p-toluenesulfonic acid monohydrate (5.1 mg, 0.027 mmol) in toluene (3.0 mL) was stirred at 85° C. overnight. The mixture was diluted with EtOAc, then washed with sat. sodium bicarbonate and brine. The organic layer was dried (Na2SO4), filtered and concentrated to give 50 mg (50%) of the desired product. LCMS calculated for C17H20N3O3S (M+H)+: m/z=346.1. Found: 346.0.

Workup

  1. washwashed with sat. sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0f496cfe55874758b35f6a8713de763e
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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