Methyl Isocyanate → 4-chloro-N-{2-[2-chloro-5-(3-methyl-ureido)-benzoyl]-5-methyl-pyridin-3-yl}-3-trifluoromethyl-benzene sulfonamide

HRID 419172Notes

Reaction equation

HRID 419172 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:36])=[C:10]([CH:35]=1)[C:11]([C:13]1[C:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)(=[O:22])=[O:21])=[CH:17][C:16]([CH3:34])=[CH:15][N:14]=1)=[O:12]>C1COCC1.CC(O)=O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][C:18]2[C:13]([C:11](=[O:12])[C:10]3[CH:35]=[C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])[CH:7]=[CH:8][C:9]=3[Cl:36])=[N:14][CH:15]=[C:16]([CH3:34])[CH:17]=2)(=[O:22])=[O:21])=[CH:24][C:25]=1[C:30]([F:33])([F:32])[F:31]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 57942517N-[2-(5-amino-2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 579426094-chloro-N-{2-[2-chloro-5-(3-methyl-ureido)-benzoyl]-5-methyl-pyridin-3-yl}-3-trifluoromethyl-benzene sulfonamideYield 38.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methylisocyanate (17 μL, 0.235 mmol) was added to N-[2-(5-amino-2-chloro-benzoyl)-5-methyl-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzene sulfonamide (59 mg, 0.117 mmol) in THF (2 mL) and AcOH (0.5 mL) and stirred at room temperature for 4 h. The reaction mixture was directly purified by preparative HPLC (20-80% acetonitrile in water) to afford 4-chloro-N-{2-[2-chloro-5-(3-methyl-ureido)-benzoyl]-5-methyl-pyridin-3-yl}-3-trifluoromethyl-benzene sulfonamide (25 mg) in 38% yield. 1H NMR (400 MHz, CDCl3+CD3OD) δ 8.14 (m, 2H), 7.95 (m, 2H), 7.63 (d, 1H), 7.58 (dd, 1H), 7.41 (dd, 1H), 7.19 (d, 1H), 2.76 (s, 3H), 2.42 (s, 3H); ESMS m/z (relative intensity): 561 (M+H)+ (100).

Workup

  1. customThe reaction mixture was directly purified by preparative HPLC (20-80% acetonitrile in water)

Sources & evidence

ORD record
ord-ad0b2477de894614983466c2399022fe
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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