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

HRID 2422879ノート

反応式

HRID 2422879 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-c6443eb4b2f64e40aedb5014d111d09a
出典データセット
uspto-grants-2011_06
特許番号
US07960365B2

反応ノート

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