2-Amino-5-chloro-3-methylbenzoic acid → 10-chloro-2-[4,5-dichloro-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-naphtho[2,3-d][1,3]oxazine-4-one

HRID 251981Notes

Reaction equation

HRID 251981 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[N:5]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6]=1[Cl:7].[NH2:18][C:19]1[C:20]([C:31](O)=[O:32])=[CH:21][C:22]2[C:27]([C:28]=1[Cl:29])=[CH:26][CH:25]=[C:24](Br)[CH:23]=2.BrC1C=C(C(O)=O)N(C2C(Cl)=CC=CN=2)C=1.NC1C(C)=CC(Cl)=CC=1C(O)=O>>[Cl:29][C:28]1[C:19]2[N:18]=[C:15]([C:4]3[N:5]([C:8]4[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=4)[C:6]([Cl:7])=[C:2]([Cl:1])[CH:3]=3)[O:17][C:31](=[O:32])[C:20]=2[CH:21]=[C:22]2[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]2

Participants

5

Reactant 4

HCID 116440442-Amino-5-chloro-3-methylbenzoic acidHCID 668542703-Amino-7-bromo-4-chloro-2-naphthoic acidHCID 668544874-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acidHCID 668545304,5-dichloro-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 5778031310-chloro-2-[4,5-dichloro-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-naphtho[2,3-d][1,3]oxazine-4-one

Procedure

According to the same manner as that of Reference Preparation Example 71-(5), 4,5-dichloro-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxylic acid and 3-amino-7-bromo-4-chloro-2-naphthoic 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 10-chloro-2-[4,5-dichloro-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-naphtho[2,3-d][1,3]oxazine-4-one of the formula:

Sources & evidence

ORD record
ord-d176981e7b294fd88206c8da225f742f
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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