3-Chloro-6-isothiocyanatotoluene → HCID 178426112, compound

HRID 1068930Notes

Reaction equation

HRID 1068930 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[S:28])=[C:22]([CH3:29])[CH:21]=1>O1CCOCC1.CN1C(=O)N(C)CC1.CS(C)=O.C(OCC)(=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:1][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=3)[NH:4][N:3]=2)=[S:28])=[C:22]([CH3:29])[CH:21]=1

Participants

6

Reactant 2

HCID 900213-Chloro-6-isothiocyanatotolueneHCID 178509242HCID 178509242, compound

Product 1

HCID 178426112HCID 178426112, compound

Reagents, catalysts & solvents 3

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 312751,4-DioxaneSolventHCID 23053668Dimethylsulfoxide ethyl acetateSolvent

Conditions

Temperature
60 °C

Procedure

With the exclusion of moisture, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6) are dissolved in 2.5 ml of dioxane and 1 ml of DMEU; 202 mg (1.1 mmol) of 4-chloro-2-methyl-phenyl isothiocyanate (Maybridge) are added and the reaction mixture is stirred overnight at RT and finally for 16 hours at 60° C. Working-up analogously to Example 66 and stirring in DMSO/ethyl acetate yield 3-[(4-chloro-2-methyl-phenyl-amino)-thiocarbonyl-amino]-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100)=12.2; FAB-MS: (M+H)+=444.

Sources & evidence

ORD record
ord-fe4e285cffcd44fb937fb9bfb220ed95
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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