HCID 66611837, 화합물 → 4-(2-(6-Methoxypyridin-3-ylamino)-5-(pyridazin-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1812168노트

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HRID 1812168 반응식
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([C:15]3[C:16]([NH:27][C:28]4[CH:29]=[N:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)=[N:17][CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][N:24]=[N:23][CH:22]=4)[CH:20]=3)[N:12]=[C:11]([CH3:36])[N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:35][O:34][C:31]1[N:30]=[CH:29][C:28]([NH:27][C:16]2[C:15]([C:13]3[N:12]=[C:11]([CH3:36])[N:10]=[C:9]([NH2:8])[N:14]=3)=[CH:20][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[N:23][CH:22]=3)=[CH:18][N:17]=2)=[CH:33][CH:32]=1

참가 물질

3

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HCID 66611837HCID 66611837, 화합물

생성물 1

HCID 595484754-(2-(6-Methoxypyridin-3-ylamino)-5-(pyridazin-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine수율 11.2%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
80 °C

실험 절차

N,N-bis(4-methoxybenzyl)-4-(2-(6-methoxypyridin-3-ylamino)-5-(pyridazin-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (140 mg, 0.223 mmol) was treated with TFA (10 mL) and fitted with a reflux condenser and heated at 80° C. for 15 h. The TFA was removed in vacuo and the residue was pipetted into an ice-cooled saturated solution of NaHCO3 resulting in a yellow suspension which was collected by filtration on a sintered glass frit. The resulting yellow solid was washed with water and MeOH dry-packed on silica gel and attempted purification on the ISCO (12 g column, 1-40% MeOH in DCM (also tried 25% 2M NH3 in MeOH in DCM)) could not liberate the desired product from silica gel. The silica gel was washed with DMSO (20 mL) and filtered through 0.45 μm acrodiscs and the DMSO removed in a Genevac over the weekend to give 4-(2-(6-methoxypyridin-3-ylamino)-5-(pyridazin-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (9.5 mg, 0.025 mmol, 10.99% yield) as a bright yellow amorphous solid. m/z (ESI, +ve ion) 388.1 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.99 (1H, s); 9.66 (1H, s); 9.25 (1H, s); 9.21 (1H, d, J=2.3 Hz); 8.91 (1H, d, J=2.3 Hz); 8.55 (1H, d, J=2.7 Hz); 8.16-8.20 (1H, m); 7.98-8.02 (1H, m); 7.92 (1H, s); 7.81 (1H, s); 6.88 (1H, d, J=8.8 Hz); 3.87 (3H, s); 2.54 (3H, s).

후처리

  1. customfitted with a reflux condenser
  2. customThe TFA was removed in vacuo
  3. temperaturecooled saturated solution of NaHCO3 resulting in a yellow suspension which
  4. filtrationwas collected by filtration on a sintered glass frit
  5. washThe resulting yellow solid was washed with water and MeOH dry-packed on silica gel
  6. custompurification on the ISCO (12 g column, 1-40% MeOH in DCM (also tried 25% 2M NH3 in MeOH in DCM)) could not
  7. washThe silica gel was washed with DMSO (20 mL)
  8. filtrationfiltered through 0.45 μm acrodiscs
  9. customthe DMSO removed in a Genevac over the weekend

출처 및 근거

ORD 기록
ord-f25388a392bd46978a16137917caa575
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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