1,2,3,4-Tetrahydroisoquinoline → HCID 23287749, compound

HRID 367173Notes

Reaction equation

HRID 367173 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:15][C:16]#[N:17].[NH4+].[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][NH:20]1>CC(C)=O.CN(C=O)C>[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[C:16]1[S:15][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[N:17]=1

Participants

7

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 23287749HCID 23287749, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.718 g (10.90 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 872 mg of ammonium thiocyanate, 15 ml of acetone, 1.52 g of 1,2,3,4-tetrahydroisoquinoline and 15 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 1.58 g of 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 57
  2. customThe resulting crude product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-350f6f5764a14d798945f0d808ad34f0
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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