Phenyl isocyanate → HCID 178523108, compound

HRID 1845750Notes

Reaction equation

HRID 1845750 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)C(=O)[O:10][N:9]=2)=[N:5][O:6][N:7]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C.C(Cl)Cl.CN(C1C=CN=CC=1)C.CO>[Cl:20][C:15]1[CH:14]=[C:13]([NH:12][C:8]([C:4]2[C:3]([CH2:2][NH:1][C:29]([NH:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:30])=[N:7][O:6][N:5]=2)=[N:9][OH:10])[CH:18]=[CH:17][C:16]=1[F:19]

Participants

7

Reactant 2

HCID 7672Phenyl isocyanateHCID 589418433-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 178523108HCID 178523108, compoundYield 164.7%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (10 mg, 0.003 mmol) was dissolved in ACN (0.2 mL) and DCM (0.2 mL). Phenyl isocyanate (7.6 mg, 0.064 mmol) DIPEA(0.012 mg, 0.096 mmol) and DMAP (0.4 mg, 0.03 mmol) were added and stirred at rt for 6 hrs. The reaction was then diluted with MeOH and purified by preparative LCMS. The intermediate was stripped to dryness, redissolved in EtOH (1 mL) and 1 M of sodium hydroxide in water (0.06 mL) was added. The reaction was stirred at rt for 1 hour, quenched with acetic acid and diluted with MeOH. The crude was purified by preparative LCMS to afford the desired product (2.0 mg). MF=C17H14ClFN6O3; LCMS calculated for C17H15ClFN6O3(M+H)+: m/z=405.1.

Workup

  1. custompurified by preparative LCMS
  2. dissolutionredissolved in EtOH (1 mL)
  3. addition1 M of sodium hydroxide in water (0.06 mL) was added
  4. stirringThe reaction was stirred at rt for 1 hour
  5. customquenched with acetic acid
  6. additiondiluted with MeOH
  7. customThe crude was purified by preparative LCMS

Sources & evidence

ORD record
ord-2abb2482706c4008afe8f3a2ae4f3e4f
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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