Hexyl isocyanate → HCID 178444873, compound

HRID 1068931Notes

Reaction equation

HRID 1068931 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.[CH2:19]([N:25]=[C:26]=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCOCC1.CN1C(=O)N(C)CC1>[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:26]([NH:25][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:27])[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 75659Hexyl isocyanateHCID 178509242HCID 178509242, compound

Product 1

HCID 178444873HCID 178444873, compound

Reagents, catalysts & solvents 2

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

Procedure

With the exclusion of moisture, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine are dissolved in 2.5 ml of dioxane and 1 ml of DMEU; 160 μl (1.1 mmol) of n-hexyl isocyanate are added and the reaction mixture is stirred overnight at RT. The dioxane is then evaporated off in a rotary evaporator and 30 ml of DIPE and 40 ml of hexane are added to the residue. Filtration with suction and washing with DIPE/hexane yield 4-(3chloro-phenylamino)-3-[(n-hexyl-amino)-carbonyl-amino]-1H-pyrazolo[3,4-d]pyrimidine; HPLC:tRet(grad20-100)=10.3; FAB-MS: (M+H)+=388.

Workup

  1. customThe dioxane is then evaporated off in a rotary evaporator and 30 ml of DIPE and 40 ml of hexane
  2. additionare added to the residue
  3. filtrationFiltration with suction
  4. washwashing with DIPE/hexane

Sources & evidence

ORD record
ord-d233253b251a4e3c953e60e50e81eab7
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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