3-Aminopyridine → HCID 25014405, 화합물

HRID 1514629노트

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HRID 1514629 반응식
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.C[N:9](C1C=CC=CC=1)[S:10]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[CH:33]=[CH:32][C:21]3=[N:22][CH:23]=[C:24]([C:26]4[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=4)[CH:25]=[C:20]3[C:19](=[O:34])[C:18]=2[CH:35]=1)(=[O:12])=[O:11].N1C=CC=C(N)C=1>CS(C)=O.O>[CH3:31][N:29]1[CH:30]=[C:26]([C:24]2[CH:25]=[C:20]3[C:19](=[O:34])[C:18]4[CH:35]=[C:14]([CH2:13][S:10]([NH:9][C:3]5[CH:1]=[N:2][CH:6]=[CH:5][CH:4]=5)(=[O:12])=[O:11])[CH:15]=[CH:16][C:17]=4[CH:33]=[CH:32][C:21]3=[N:22][CH:23]=2)[CH:27]=[N:28]1

참가 물질

6

반응물 3

HCID 100093-AminopyridineHCID 13387N-methyl-2-pyrrolidoneHCID 25014404HCID 25014404, 화합물

생성물 1

HCID 25014405HCID 25014405, 화합물

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
180 °C

실험 절차

N-Methyl-2-pyrrolidinone (3 ml) was added to N-methyl-1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-phenylmethanesulfonamide (150 mg, 0.319 mmol) and pyridin-3-amine (150 mg, 1.594 mmol) in a vial. The vial was sealed and the resulting solution was heated to 180° C. with stirring. After 2.25 h., the reaction was cooled to room temperature and diluted in DMSO and water. The resulting solution was filtered and purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford the title compound as a brown solid. 1H NMR (600 MHz, DMSO-D6) δ 9.21 (d, 1H); 8.52 (d, 1H); 8.48 (s, 1H); 8.33 (d, 1H); 8.16 (d, 1H); 8.15 (s, 1H); 8.07 (s, 1H); 7.77 (d, 1H); 7.68 (dd, 1H); 7.52 (m, 1H); 7.35 (d, 1H); 7.32 (d, 1H); 7.25 (m, 1H); 4.77 (s, 2H); 3.89 (s, 3H). LRMS (APCI) calculated for C24H19N5O3S [M+H]+, 458.1. found 458.1.

후처리

  1. customThe vial was sealed
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationThe resulting solution was filtered
  4. custompurified by preparative HPLC Reverse phase (C-18)
  5. washeluting with Acetonitrile/Water+0.05% TFA

출처 및 근거

ORD 기록
ord-595b6b6acae9408f95d3fe6b56e0e0b0
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222269B2

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