Benzene, 1-chloro-3-isocyanato- → HCID 178522045, compound

HRID 1068929Notes

Reaction equation

HRID 1068929 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:21]=[C:22]([N:26]=[C:27]=[O:28])[CH:23]=[CH:24][CH:25]=1.N1C2C=NC=NC=2C=N1>O1CCOCC1.CN1C(=O)N(C)CC1.C(O)C>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][C:27]([NH:26][C:22]4[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=4)=[O:28])[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 17968Benzene, 1-chloro-3-isocyanato-2×HCID 210839761H-pyrazolo(4,3-d)pyrimidineHCID 178509242HCID 178509242, compound

Product 1

HCID 178522045HCID 178522045, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 312751,4-DioxaneSolvent

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; 137 I (1.1 mmol) of 3-chloro-phenyl isocyanate are added and the reaction mixture is stirred overnight at RT and finally for 16 hours at 60° C. Since, according to HPLC, not all of the pyrazolo-pyrimidine has reacted, a further 40 all of 3chloro-phenyl isocyanate are added and the mixture is stirred for a further 20 hours at 60° C. Working-up analogously to Example 66 and stirring in hot ethanol yield 4-(3-chloro-phenylamino)-3-[(3-chloro-phenyl-amino)-carbonylamino]-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100)=12.4; FARMS: (M+H)+=414.

Workup

  1. stirringthe mixture is stirred for a further 20 hours at 60° C

Sources & evidence

ORD record
ord-00d32a0937114bddbc63717e4348ee98
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

Loading…