Benzoic acid, 3-amino-, methyl ester → Methyl 3-{[(2,5-difluorophenyl)sulfonyl]amino}benzoate

HRID 1670907Notes

Reaction equation

HRID 1670907 reaction equation
ClC1N=C(/C=C(/C2C=C(NS(C3C(F)=CC=CC=3F)(=O)=O)C=CC=2)\O)C=CN=1.[NH2:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35][CH3:36])=[O:34].[F:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:42]=1[S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl>[F:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:42]=1[S:48]([NH:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35][CH3:36])=[O:34])(=[O:50])=[O:49]

Participants

5

Reactant 3

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 136176025N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 16344470Methyl 3-{[(2,5-difluorophenyl)sulfonyl]amino}benzoateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a procedure analogous to the procedure described in Intermediate 5, Step A using methyl 3-aminobenzoate (16 g, 105.9 mmol) in DCM (150 mL) and 2,5-difluorobenzene-1-sulfonyl chloride (24.7 g, 116.5 mmol) the title compound was obtained (25.6 g, 73.8% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.06-11.13 (br, 1H), 7.42-7.52 (m, 2H), 7.52-7.77 (m, 4H), 7.78-7.80 (m, 1H), 3.88 (s, 3H).

Sources & evidence

ORD record
ord-9989e4912bb84900a35c9b9b3c0a296b
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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