Propyl isocyanate → HCID 23154983, compound

HRID 1912833Notes

Reaction equation

HRID 1912833 reaction equation
Cl.[NH2:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:23]=2)=[O:20])=[CH:14][CH:13]=1.[CH2:33]([N:36]=[C:37]=[O:38])[CH2:34][CH3:35]>N1C=CC=CC=1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19](=[O:20])[NH:18][C:15]2[CH:14]=[CH:13][C:12]([N:7]3[CH:6]=[N:5][C:4]4[C:8]3=[N:9][CH:10]=[N:11][C:3]=4[NH:2][C:37]([NH:36][CH2:33][CH2:34][CH3:35])=[O:38])=[CH:17][CH:16]=2)=[CH:23][C:24]=1[C:29]([F:31])([F:32])[F:30]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 231551201-[4-(6-Aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride

Product 1

HCID 23154983HCID 23154983, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

In 10 mL of pyridine, 300 mg (0.62 mmol) of 1-[4-(6-aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride was dissolved, and 1.58 g (18.6 mmol) of propyl isocyanate was added thereto and the mixture solution was stirred at 50° C. for eight hours. The reaction solution was concentrated under reduced pressure, and then the residue was partitioned between ethyl acetate and water, and the organic layer was washed with a saturated sodium chloride solution, dried and concentrated. The residue was triturated with n-hexane:ethyl acetate=1:1, collected by filtration and vacuum dried to obtain 210 mg (64%) of 1-(9-(4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl)-9H-purin-6-yl)-3-propylurea (Table 1, Compound No. 119) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with a saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was triturated with n-hexane
  7. filtrationethyl acetate=1:1, collected by filtration and vacuum
  8. customdried

Sources & evidence

ORD record
ord-ce67cc46fb24449d9fe27189f4d89a15
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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