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

HRID 2422879노트

반응식

HRID 2422879 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27945611-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonyl chlorideHCID 672458741-(3,5'-Difluoro-2'-methoxy-biphenyl-4-yl)-ethylamine

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-c6443eb4b2f64e40aedb5014d111d09a
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960365B2

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