(RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine → (RS)-6-Hydroxymethyl-5-[(isoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 443838Notes

Reaction equation

HRID 443838 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)=[C:2]=[S:3].[OH:14][CH2:15][CH:16]1[NH:21][CH2:20][C:19]2[CH:22]=[CH:23][S:24][C:18]=2[CH2:17]1>C(O)C>[OH:14][CH2:15][CH:16]1[N:21]([C:2](=[S:3])[NH:1][C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]=2[CH:6]=[CH:7][N:8]=[CH:9]3)[CH2:20][C:19]2[CH:22]=[CH:23][S:24][C:18]=2[CH2:17]1

Participants

4

Reactant 2

HCID 12939919(RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 130143205-Isothiocyanatoisoquinoline

Product 1

HCID 12939922(RS)-6-Hydroxymethyl-5-[(isoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridineYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Isothiocyanatoisoquinoline (5.1 g) is added to a solution of (RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (4.3 g) in absolute ethanol (55 cc). After 48 hours at a temperature of about 20° C., the resulting crystals are filtered off, washed with diisopropyl ether (75 cc) and then dried at 40° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). (RS)-6-Hydroxymethyl-5-[(isoquinol-5-yl)thiocarbamoyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (6.7 g), melting at 185° C., is thus obtained.

Workup

  1. filtrationthe resulting crystals are filtered off
  2. washwashed with diisopropyl ether (75 cc)
  3. customdried at 40° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-353b0d9b32ed4da48e23f2bd30c6b633
Source dataset
uspto-grants-1981_04
Patent number
US04261999

Reaction notes

Loading…