Isopropyl isocyanate → HCID 57717573, compound

HRID 2283825Notes

Reaction equation

HRID 2283825 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]([CH3:28])([CH3:27])[CH2:9][C:10]1[N:11]([CH2:24][CH2:25][CH3:26])[N:12]=[C:13]2[C:22]=1[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:15]=[C:14]2[NH2:23]>ClCCl>[NH2:23][C:14]1[C:13]2=[N:12][N:11]([CH2:24][CH2:25][CH3:26])[C:10]([CH2:9][C:8]([NH:7][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])([CH3:27])[CH3:28])=[C:22]2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 57717565HCID 57717565, compound

Product 1

HCID 57717573HCID 57717573, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl isocyanate (255 mg, 3.00 mmol) was added to a 0° C. stirred solution of 1-(2-amino-2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 64, 892 mg, 3.00 mmol) in dichloromethane (26.7 mL). After 4 hours at 0° C., the solution was stirred overnight at ambient temperature. The solution was concentrated to afford a colorless resin that was purified by IFC (silica gel, elution with CMA in chloroform). The appropriate fractions were combined and concentrated to yield a solid that was recrystallized from ethyl acetate in hexanes. The solid was isolated by filtration, washed with ethyl acetate/hexanes, and dried to yield 130 mg of N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]-N′-isopropylurea as a white solid, mp 190-191° C.

Workup

  1. concentrationThe solution was concentrated
  2. customto afford a colorless resin that
  3. customwas purified by IFC (silica gel, elution with CMA in chloroform)
  4. concentrationconcentrated
  5. customto yield a solid
  6. customthat was recrystallized from ethyl acetate in hexanes
  7. customThe solid was isolated by filtration
  8. washwashed with ethyl acetate/hexanes
  9. customdried

Sources & evidence

ORD record
ord-9456da65488747d89c640e4a1e0f8c3e
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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