Triethylamine → 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonic acid [1-(3,5'-difluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide

HRID 2422879Notes

Reaction equation

HRID 2422879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]([NH2:10])[CH3:9].C(N(CC)CC)C.[CH3:27][N:28]1[CH:32]=[C:31]([S:33](Cl)(=[O:35])=[O:34])[C:30]([C:37]([F:40])([F:39])[F:38])=[N:29]1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]([NH:10][S:33]([C:31]1[C:30]([C:37]([F:40])([F:38])[F:39])=[N:29][N:28]([CH3:27])[CH:32]=1)(=[O:35])=[O:34])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27945611-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonyl chlorideHCID 67245874HCID 67245874, compound

Product 1

HCID 672454371-Methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonic acid [1-(3,5'-difluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amideYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3,5′-Difluoro-2′-methoxy-biphenyl-4-yl)-ethylamine was prepared in a similar manner to 1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (Example 34) using 4′-bromo-2′-fluoroacetophenone to give 1-(4-bromo-2-fluoro-phenyl)-ethylamine. To a solution of 1-(3,5′-difluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (20.0 mg, 0.08 mmol) in dichloromethane (1 ml) was added triethylamine (8.1 mg, 0.08 mmol) and 1-methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonyl chloride (14.2 mg, 0.06 mmol). The solution was stirred overnight then the solvent evaporated and the residue purified by flash chromatography over silica gel eluting with dichloromethane. Evaporation of solvent under reduced pressure gave the title compound (20 mg). 1H NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 7.21-7.16 (m, 2H), 7.14-7.09 (m, 1H), 7.05-6.95 (m, 2H), 6.93-6.88 (m, 1H), 5.11 (d, 1H), 4.76 (dq, 1H), 3.81 (s, 3H), 3.73 (s, 3H), 1.55 (d, 3H) ppm; MS (ESI) m/z: 498.3 [M+Na]+.

Workup

  1. customthe solvent evaporated
  2. customthe residue purified by flash chromatography over silica gel eluting with dichloromethane
  3. customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-c6443eb4b2f64e40aedb5014d111d09a
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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