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

HRID 251988Notes

Reaction equation

HRID 251988 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[N:5]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=1.[NH2:18][C:19]1[C:27]([Br:28])=[CH:26][C:25]([Br:29])=[CH:24][C:20]=1[C:21](O)=[O:22].BrC1C=C(C(O)=O)N(C2C(Cl)=CC=CN=2)C=1.NC1C(C)=CC(Cl)=CC=1C(O)=O>>[Br:29][C:25]1[CH:26]=[C:27]([Br:28])[C:19]2[N:18]=[C:15]([C:4]3[N:5]([C:7]4[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][N:8]=4)[CH:6]=[C:2]([Br:1])[CH:3]=3)[O:17][C:21](=[O:22])[C:20]=2[CH:24]=1

Participants

5

Reactant 4

HCID 2194912-Amino-3,5-dibromobenzoic acidHCID 116440442-Amino-5-chloro-3-methylbenzoic acidHCID 668541524-bromo-1-(3-cyano-2-pyridinyl)-1H-pyrrole-2-carboxylic acidHCID 668544874-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 668539936,8-dibromo-2-[4-bromo-1-(3-cyano-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-cyano-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-cyano-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one of the formula:

Sources & evidence

ORD record
ord-f1190df80bd74866b15f1d129ebc4b42
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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