5-Chlorothiophene-2-Sulfonamide → HCID 11634654, compound

HRID 1271065Notes

Reaction equation

HRID 1271065 reaction equation
[F:1][C:2]1[C:3]([NH:22][CH3:23])=[CH:4][C:5]2[O:10][CH2:9][N:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:21]=1.Cl.CN(C)CCCN=C=NCC.[Cl:36][C:37]1[S:41][C:40]([S:42]([NH2:45])(=[O:44])=[O:43])=[CH:39][CH:38]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:36][C:37]1[S:41][C:40]([S:42]([NH:45][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][C:11]([N:8]3[C:7](=[O:20])[C:6]4[CH:21]=[C:2]([F:1])[C:3]([NH:22][CH3:23])=[CH:4][C:5]=4[O:10][CH2:9]3)=[CH:12][CH:13]=2)(=[O:44])=[O:43])=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 12413015-Chlorothiophene-2-SulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18452500HCID 18452500, compound

Product 1

HCID 11634654HCID 11634654, compoundYield 160%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 4-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)benzoic acid (0.02 g, 0.063 mmol) in methylene chloride (2 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.013 g, 0.068 mmol), N,N-dimethylpyridin-4-amine (0.008 g, 0.068 mmol) followed by 5-chlorothiophene-2-sulfonamide (0.014 g, 0.07 mmol) and the mixture stirred at room temperature for 8 hr. The solvent was removed and the product purified on HPLC (C18) to give N-(5-chlorothiophen-2-ylsulfonyl)-4-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e] [1,3] oxazin-3(4H)-yl) benzamide (0.05 g, 15%). RP-HPLC: 2.58 min; ES-MS (M+H)+=496.0; 1H-NMR (MeOH-d4) δ (ppm): 2.8 (s, 3), 5.6 (s, 2), 6.2 (d, 1), 7.1 (d, 1), 7.3 (d, 1), 7.4 (d, 2), 7.7 (d, 1), 7.9 (d, 2).

Workup

  1. customThe solvent was removed
  2. customthe product purified on HPLC (C18)

Sources & evidence

ORD record
ord-45cba94d3e834cceaba4601da52ad8f6
Source dataset
uspto-grants-2007_04
Patent number
US07205296B2

Reaction notes

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