Acetyl chloride → HCID 18916382, compound

HRID 1290621Notes

Reaction equation

HRID 1290621 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[C:10]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]3=[O:23])=[C:9]([F:24])[CH:8]=[C:7]([Cl:25])[C:5]=2[N:6]=1.[C:26](Cl)(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:26]([NH:1][C:2]1[O:3][C:4]2[C:10]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[N:13]([CH3:22])[C:12]3=[O:23])=[C:9]([F:24])[CH:8]=[C:7]([Cl:25])[C:5]=2[N:6]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 18916387HCID 18916387, compound

Product 1

HCID 18916382HCID 18916382, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Additional moieties may also be added to the benzoxazole ring at this point. For example, bromine moieties are added to 3-(2-methyl-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione by reacting it with N-bromosuccinimide under basic conditions, yielding the corresponding 3-(2-dibromomethyl-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (VB). An alkyl group can also be added to 3-(2-thio-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione by reacting it with an alkyl halide in the manner described previously, yielding the appropriate 3-(2-alkylthio-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (VC). In addition, (V), where R in the 2-position is amino may be further reacted to add additional moieties to the amine. For example, an acetyl moiety is added to 3-(2-amino-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione by reacting it with acetyl chloride in the presence of pyridine affording 3-(2-acetylamino-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (VD). The so-prepared pyrimidinedione (VD) is in turn reacted with sodium hydride and methanesulfonyl chloride to form the appropriate 3-[2-(N-acetyl-N-methylsulfonylamino)-disubstituted-benzoxazol-7-yl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (VE), which is hydrogenated under acidic conditions affording 3-(2-methylsulfonylamino-disubstituted-benzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (VF). The pyrimidinedione (VF) is in turn alkylated in the manner described previously, affording 3-[2-(N-alkyl-N-methylsulfonyl-amino)-disubstituted-benzoxazol-7-yl]-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (VG). Examples 14, 17, 20, 21, 22, and 23 provide the detailed procedures for this route.

Workup

  1. custommay be further reacted

Sources & evidence

ORD record
ord-3925d570c8fa4ad8b34cd4e1ab242c14
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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