Sodium Hydroxide → HCID 11428427, compound

HRID 2102784Notes

Reaction equation

HRID 2102784 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10](=O)[CH:9]([CH:12]=O)[CH2:8][CH2:7][C:5]=2[N:6]=1.[N+]([O-])(O)=O.[F:18][C:19]([F:31])([F:30])[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:22][CH:21]=1.[OH-].[Na+]>COCCO>[CH3:1][C:2]1[S:3][C:4]2[C:10]3[N:29]=[C:27]([NH:26][C:23]4[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:30])[F:31])=[CH:25][CH:24]=4)[N:28]=[CH:12][C:9]=3[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 248876322-Methyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carbaldehydeHCID 178512498HCID 178512498, compound

Product 1

HCID 11428427HCID 11428427, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 2-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazole-6-carbaldehyde (200 mg, 1.02 mmol), N-(4-trifluoromethyl-phenyl)-guanidine nitrate (273 mg, 1.02 mmol), NaOH (41 mg, 1.02 mmol) and 2-methoxyethanol (1.25 mL) was heated under reflux for 16 h. The reaction mixture was concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) followed by crystallisation from EtOAc gave the pure title compound as a white crystalline solid (30 mg, 8%): mp 212-213° C. Anal. RP-HPLC: tR 21.8 min (10-70% MeCN, purity 95%). 1H-NMR (CDCl3): δ 8.17 (s, 1H, Py-H), 7.71 (d, 2H, J 8.4, Ph-H), 7.52 (d, 2H, J 8.4, Ph-H), 7.16 (s, 1H, NH), 3.04 (t, 2H, J 6.6, CH2), 2.94 (t, 2H, J 6.6, CH2), 2.72 (s, 3H, CH3). MS (ESI−): m/z 360.95 (M−H)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customFlash column chromatography (20% EtOAc:hexane) followed by crystallisation from EtOAc

Sources & evidence

ORD record
ord-840894b458c343dc9b30b47f67616051
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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