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

HRID 252006Notes

Reaction equation

HRID 252006 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([S:13][C:14]#[N:15])=[CH:11][CH:10]=[C:9]2[C:16]([OH:18])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:19][C:20]1[C:28]([Br:29])=[CH:27][C:26]([Br:30])=[CH:25][C:21]=1[C:22](O)=[O:23].BrC1C=C(C(O)=O)N(C2C(Cl)=CC=CN=2)C=1.NC1C(C)=CC(Cl)=CC=1C(O)=O>>[Br:30][C:26]1[CH:27]=[C:28]([Br:29])[C:20]2[N:19]=[C:16]([C:9]3[N:8]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=4)[C:12]([S:13][C:14]#[N:15])=[CH:11][CH:10]=3)[O:18][C:22](=[O:23])[C:21]=2[CH:25]=1

Participants

5

Reactant 4

HCID 2194912-Amino-3,5-dibromobenzoic acidHCID 116440442-Amino-5-chloro-3-methylbenzoic acidHCID 668544874-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acidHCID 866325641-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrole-2-carboxylic acid

Product 1

HCID 866325636,8-dibromo-2-[1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one

Procedure

According to the same manner as that of Reference Preparation Example 71-(5), 1-(3-chloro-2-pyridinyl)-5-thiocyanato-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-[1-(3-chloro-2-pyridinyl)-5-thiocyanato-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one of the formula:

Sources & evidence

ORD record
ord-45a080e80bf148ffb275b2eec2168784
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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