3-Pyridinemethanamine → 6-(2-cyanophenyl)-4-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2074437노트

반응식

HRID 2074437 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:19]=[C:18]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]=1)#[N:2].[NH2:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.C[Al](C)C>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:19]=[C:18]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[C:12]([C:13]([NH:30][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:14])=[CH:11][N:10]=1)#[N:2]

참가 물질

5

반응물 3

HCID 310183-PyridinemethanamineHCID 16682925TrimethylaluminumHCID 59744986Ethyl 6-(2-cyanophenyl)-4-(3-fluorophenethylamino)nicotinate

생성물 1

HCID 597449876-(2-cyanophenyl)-4-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide수율 8.6%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
70 °C

실험 절차

To a solution of ethyl 6-(2-cyanophenyl)-4-(3-fluorophenethylamino)nicotinate (100 mg, 0.26 mmol) and 3-aminomethylpyridine (39 mg, 0.36 mmol) in toluene (1 mL) was added AlMe3 (0.2 mL, 2M in toluene, 0.39 mmol) at r.t. The reaction mixture was stirred at 70° C. overnight. The reaction was cooled, quenched with sat. NaHCO3, and diluted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give a crude oil. The crude mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O to give 6-(2-cyanophenyl)-4-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (10 mg, 8.6%). LRMS (M+H+) m/z 452.0.

후처리

  1. temperatureThe reaction was cooled
  2. customquenched with sat. NaHCO3
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a crude oil
  10. customThe crude mixture was purified on RP-HPLC
  11. additiona mixture of acetonitrile and H2O

출처 및 근거

ORD 기록
ord-d73ff215eb6546039d20e2664de9cc89
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919511B2

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