1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67717624, compound

HRID 1290640Notes

Reaction equation

HRID 1290640 reaction equation
[CH3:1][O:2][C:3]([C:6]1[O:7][C:8]2[C:14]([NH:15][C:16](=O)[O:17]CC)=[C:13]([F:21])[CH:12]=[C:11]([Cl:22])[C:9]=2[N:10]=1)([CH3:5])[CH3:4].C[O-].[Na+].[NH2:26]/[C:27](/[C:34]([F:37])([F:36])[F:35])=[CH:28]\[C:29]([O:31]CC)=O.N12CCCN=C1CCCCC2>CN(C)C=O>[CH3:1][O:2][C:3]([C:6]1[O:7][C:8]2[C:14]([N:15]3[C:29](=[O:31])[CH:28]=[C:27]([C:34]([F:35])([F:36])[F:37])[NH:26][C:16]3=[O:17])=[C:13]([F:21])[CH:12]=[C:11]([Cl:22])[C:9]=2[N:10]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 10942334Sodium MethoxideHCID 18916392HCID 18916392, compound

Product 1

HCID 67717624HCID 67717624, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An additional 0.6 gram of 3-[2-(1-methoxy-1-methylethyl)-4-chloro-6-fluorobenzoxazol-7-yl)-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione was prepared in the manner of Step E, Example 1, with 0.8 gram (2.4 mmole) of ethyl N-[2-(1-methoxy-1-methylethyl)-4-chloro-6-fluorobenzoxazol-7-yl]carbamate, 0.15 gram (2.8 mmole) of sodium methoxide, 0.44 gram (2.4 mmole) of ethyl 3-amino-4,4,4-trifluorocrotonate, 30 mL of N,N-dimethylformamide, arid 0.37 gram (2.4 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene as reagents. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-25a093daf65646fdb26e17b86ffddb71
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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