p-Toluenesulfonic acid → HCID 10092936, compound

HRID 1085151Notes

Reaction equation

HRID 1085151 reaction equation
[CH3:1][C:2]1[C:29]([CH3:30])=[CH:28][C:5]2[NH:6][C:7](=S)[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1.O.[NH2:32][NH2:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CCC>[CH3:1][C:2]1[C:29]([CH3:30])=[CH:28][C:5]2[N:6]=[C:7]([NH:32][NH2:33])[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 24654Hydrazine hydrate (1:1)HCID 10024618HCID 10024618, compound

Product 1

HCID 10092936HCID 10092936, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,3-dihydro-7,8-dimethyl-4-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]-1H-[1,5]benzodiazepine-2-thione (411 mg, 1.0 mmol), hydrazine hydrate (60 mg, 1.2 mmol) and p-toluenesulphonic acid (10 mg) in n-butanol (5 ml) was heated at 100° C. for 1.5 hours. The solvent was removed under reduced pressure and the crude product was used directly for Examples 29-31.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8515e2e5b41647659c005ab25e2be9c0
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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