2-Chloro-5-methoxybenzene-1-sulfonamide → N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxamide

HRID 570180Notes

Reaction equation

HRID 570180 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:8]=1.Cl.CN(C)CCCN=C=NCC.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[S:38]([NH2:41])(=[O:40])=[O:39]>CN(C)C1C=CN=CC=1.C(O)(C)(C)C.ClCCl>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[S:38]([NH:41][C:12]([C:10]1[N:11]=[C:6]2[CH:5]=[N:4][C:3]([C:2]([F:1])([F:16])[F:15])=[CH:8][N:7]2[CH:9]=1)=[O:14])(=[O:40])=[O:39]

Participants

7

Reactant 3

HCID 3140422-Chloro-5-methoxybenzene-1-sulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675171956-(Trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylic acid

Product 1

HCID 56952251N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxamideYield 49.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To the product of Step B (120 mg, 0.52 mmol) was added a solution of 4-(dimethylamino)pyridine (183 mg, 1.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (248 mg, 1.3 mmol) in t-butanol (5 mL) and dichloromethane (5 mL). The reaction mixture was stirred for 15 minutes, 2-chloro-5-methoxybenzenesulfonamide (92 mg, 0.41 mmol) was added, and stirring was continued at room temperature overnight. Dichloromethane (100 mL) was then added, the mixture was washed with 1 N hydrochloric acid (3×100 mL), and the combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure to afford a solid. The solid was rinsed with diethyl ether and dried to afford. 89 mg of the title compound, a compound of this invention, as a white solid, m.p. 236-237° C. 1H NMR (CDCl3) δ 9.99 (br s, 1H), 9.23 (s, 1H), 8.56 (s, 1H), 8.32 (s, 1H), 7.86 (s, 1H), 7.37 (d, 1H), 7.10 (dd, 1H) 3.91 (s, 3H).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. washthe mixture was washed with 1 N hydrochloric acid (3×100 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford a solid
  7. washThe solid was rinsed with diethyl ether
  8. customdried
  9. customto afford

Sources & evidence

ORD record
ord-c01c978631964ef3a4df3831bb722792
Source dataset
uspto-grants-2015_05
Patent number
US09023850B2

Reaction notes

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