Methylamine → 3-(4-Fluorophenyl)-5-(4-(4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo(2.2.2)octan-1-yl)-1,2,4-oxadiazole

HRID 1784500노트

반응식

HRID 1784500 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]34[CH2:20][CH2:19][C:16]([C:21]5O[C:23]([C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=6[C:32]([F:35])([F:34])[F:33])=[N:24][N:25]=5)([CH2:17][CH2:18]3)[CH2:15][CH2:14]4)[O:10][N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH3:43][NH2:44]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]34[CH2:14][CH2:15][C:16]([C:21]5[N:44]([CH3:43])[C:23]([C:26]6[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=6[C:32]([F:34])([F:35])[F:33])=[N:24][N:25]=5)([CH2:19][CH2:20]3)[CH2:17][CH2:18]4)[O:10][N:9]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6329Methylamine2회HCID 6422Trifluoroacetic acidHCID 225916773-(4-Fluorophenyl)-5-(4-{5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo [2.2.2]oct-1-yl)-1,2,4-oxadiazole

생성물 1

HCID 115261473-(4-Fluorophenyl)-5-(4-(4-methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo(2.2.2)octan-1-yl)-1,2,4-oxadiazole

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of above 1,2,4-oxadiazole (7-E) (115.2 mg, 0.238 mmol) and the trifluoroacetic acid salt of methylamine (1.73 g, 11.9 mmol) in a 2M solution of methylamine in methanol (4 mL) was heated at 150° C. in a sealed tube for 48 h. The mixture was then concentrated, and the residue was taken up in dichloromethane, washed with saturated sodium bicarbonate aqueous solution. The organics were concentrated and the residue was purified using reverse-phase HPLC with TFA-buffered acetonitrile/water (40-80%) as eluent. The fractions containing the product were combined, neutralized with saturated sodium bicarbonate aqueous solution and lyophilized from acetonitrile/water to provide 3-(4-fluorophenyl)-5-(4-{4-methyl-5-[2-(trifluoromethyl)phenyl]4H-1,2,4-triazol-3-yl}bicyclo[2.2.2]oct-1-yl)-1,2,4-oxadiazole (7-F). 1HNMR (CDCl3) δ 2.25-2.35 (m, 12H), 3.53 (s, 3H), 7.21 (t, J=8.7 Hz, 2H), 7.54 (m, 1H), 7.73 (m, 2H), 7.88 (m, 1H), 8.13 (m, 2H). ESI-MS m/z (M+H) 498.2.

후처리

  1. concentrationThe mixture was then concentrated
  2. washwashed with saturated sodium bicarbonate aqueous solution
  3. concentrationThe organics were concentrated
  4. customthe residue was purified
  5. additionThe fractions containing the product

출처 및 근거

ORD 기록
ord-9ffb1b09c9654cf0ab8b97de94dde1ea
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504402B2

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