Urea → HCID 45482159, compound

HRID 1366108Notes

Reaction equation

HRID 1366108 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].C(Cl)(Cl)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)(OC1C=CC=CC=1)N.N[CH2:44][CH2:45][N:46]1[C:55]2[C:50](=[CH:51][CH:52]=[C:53]([NH:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:66])[F:65])[CH:59]=3)[CH:54]=2)[N:49]=[C:48]([CH3:68])[C:47]1=[O:69].CN1CCOCC1>C1COCC1>[CH3:68][C:48]1[C:47](=[O:69])[N:46]([CH2:45][CH2:44][NH:1][C:2]([NH2:4])=[O:3])[C:55]2[C:50]([N:49]=1)=[CH:51][CH:52]=[C:53]([NH:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:66])[F:65])[CH:59]=1)[CH:54]=2

Participants

9

Reactant 7

HCID 1176UreaHCID 6371PhosgeneHCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 69322Phenyl carbamate2×HCID 94429TriphosgeneHCID 59822525HCID 59822525, compound

Product 1

HCID 45482159HCID 45482159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compounds of Formula I in which R1 includes a urea moiety can be synthesized from primary amines in a variety of ways using phosgene, triphosgene, carbonyldiimidazole, and others as coupling reagents. One preferred way includes the use of the reagent phenyl carbamate (Young, R. J. et al, Bioorg. Med. Chem. Lett. 2006, 16, 5953-7). Starting material 1-(2-aminoethyl)-3-methyl-7-(3-(trifluoromethyl)benzyl-amino)quinoxalin-2(1H)-one (50 mg) was heated to reflux in THF for 2 h in the presence of N-methyl morpholine (0.16 mmol) and phenyl carbamate (0.16 mmol). The reaction mixture was concentrated and purified by chromatography using 6% MeOH in dichloromethane as eluent. Product 1-(2-(3-methyl-2-oxo-7-(3-(trifluoromethyl)benzyl-amino)quinoxalin-1(2H)-yl)ethyl)urea was isolated as off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography

Sources & evidence

ORD record
ord-53fbb87b81af4f27bd0946436a5d7b74
Source dataset
uspto-grants-2011_02
Patent number
US07893066B2

Reaction notes

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