5-Chloro-2-methoxybenzene-1-sulfonyl chloride → HCID 66789161, compound

HRID 1360273Notes

Reaction equation

HRID 1360273 reaction equation
COC(=O)C1C=CC(NC(=O)C2C=CC(O)=C(N)C=2)=NC=1.[CH3:22][O:23][C:24](=[O:44])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][C:37]3[O:42][CH2:41][CH2:40][NH:39][C:38]=3[CH:43]=2)=[O:33])=[N:27][CH:26]=1.[Cl:45][C:46]1[CH:47]=[CH:48][C:49]([O:56][CH3:57])=[C:50]([S:52](Cl)(=[O:54])=[O:53])[CH:51]=1>>[CH3:22][O:23][C:24](=[O:44])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][C:37]3[O:42][CH2:41][CH2:40][N:39]([S:52]([C:50]4[CH:51]=[C:46]([Cl:45])[CH:47]=[CH:48][C:49]=4[O:56][CH3:57])(=[O:53])=[O:54])[C:38]=3[CH:43]=2)=[O:33])=[N:27][CH:26]=1

Participants

4

Reactant 3

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 66789133HCID 66789133, compoundHCID 66789327HCID 66789327, compound

Product 1

HCID 66789161HCID 66789161, compound

Procedure

6-{[4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-nicotinic acid, MS (ISP): m/e=502.1 (M−H), was prepared as described for example 14, steps 1 to 8. Step 4 was performed using 6-amino-nicotinic acid methyl ester, yielding 6-(4-benzyloxy-3-nitro-benzoylamino)-nicotinic acid methyl ester, which was reduced to 6-(3-amino-4-hydroxy-benzoylamino)-nicotinic acid methyl ester in step 5 and cyclized to 6-[(3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl)-amino]-nicotinic acid methyl ester in step 6. Step 7 was performed using 5-chloro-2-methoxy-benzenesulfonyl chloride and yielded 6-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-nicotinic acid methyl ester, which was hydrolyzed in step 8.

Sources & evidence

ORD record
ord-85dd99842b264e4da12c6425600525c5
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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