p-Toluenesulfonic acid monohydrate → HCID 18506792, compound

HRID 1355549Notes

Reaction equation

HRID 1355549 reaction equation
CO[C:3](OC)([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:4][NH:5][C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=1)=[S:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:15][C:14]1[C:9]([NH:8][C:6]2[S:7][C:3]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[CH:4][N:5]=2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18506825HCID 18506825, compound

Product 1

HCID 18506792HCID 18506792, compound

Conditions

Temperature
140 °C

Procedure

1-(2,2-Dimethoxy-2-pyridin-4-yl-ethyl)-3-(3-methyl-pyridin-2-yl)-thiourea (19-2, 0.050 g, 0.16 mmol) and p-toluenesulfonic acid monohydrate (0.003 g, 0.02 mmol) were combined and heated to 140° C. The reaction was terminated at partial conversion and was purified by reverse phase HPLC to provide the titled compound. 1H NMR (CD3OD) δ 8.61 (d, 2H, J=7.1 Hz), 8.48 (s, 1H), 8.30 (dd, 1H, J=1.0, 4.8 Hz), 8.15 (d, 2H, J=7.3 Hz), 7.74 (dd, 1H, J=0.7, 7.3 Hz), 7.10 (dd, 1H, J=5.1, 7.3 Hz), 2.43 (s, 3H).

Workup

  1. customThe reaction was terminated at partial conversion
  2. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b5cf53745ff04883ae52260425cd731f
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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