2-Amino-3,5-dibromobenzoic acid → 6,8-dibromo-2-[4-bromo-1-(3-trifluoromethyl-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one

HRID 251989Notes

Reaction equation

HRID 251989 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17]([OH:19])=O)[N:5]([C:7]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=1.[NH2:20][C:21]1[C:29]([Br:30])=[CH:28][C:27]([Br:31])=[CH:26][C:22]=1[C:23](O)=[O:24].BrC1C=C(C(O)=O)N(C2C(Cl)=CC=CN=2)C=1.NC1C(C)=CC(Cl)=CC=1C(O)=O>>[Br:31][C:27]1[CH:28]=[C:29]([Br:30])[C:21]2[N:20]=[C:17]([C:4]3[N:5]([C:7]4[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:10]=[CH:9][N:8]=4)[CH:6]=[C:2]([Br:1])[CH:3]=3)[O:19][C:23](=[O:24])[C:22]=2[CH:26]=1

Participants

5

Reactant 4

HCID 2194912-Amino-3,5-dibromobenzoic acidHCID 116440442-Amino-5-chloro-3-methylbenzoic acidHCID 668540984-bromo-1-(3-trifluoromethyl-2-pyridinyl)-1H-pyrrole-2-carboxylic acidHCID 668544874-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 866325586,8-dibromo-2-[4-bromo-1-(3-trifluoromethyl-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one

Procedure

According to the same manner as that of Reference Preparation Example 71-(5), 4-bromo-1-(3-trifluoromethyl-2-pyridinyl)-1H-pyrrole-2-carboxylic acid and 2-amino-3,5-dibromobenzoic acid were used in place of 4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid and 2-amino-5-chloro-3-methylbenzoic acid respectively to obtain 6,8-dibromo-2-[4-bromo-1-(3-trifluoromethyl-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one of the formula:

Sources & evidence

ORD record
ord-0ef1d4248feb43bf94b6713dad422d0c
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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