Benzeneethanamine, alpha-methyl-, phosphate (1:1) → 4-(5-(Benzyloxy)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621776

반응식

HRID 1621776 반응식
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:3]=1.[CH2:28]([O:35][C:36]1[CH:37]=[C:38](B(O)O)[C:39]([F:42])=[N:40][CH:41]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(N)CC1C=CC=CC=1.OP(O)(O)=O.C([O-])(=O)C.[K+]>O.CCO>[CH2:28]([O:35][C:36]1[CH:37]=[C:38]([C:2]2[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[N:3]=2)[C:39]([F:42])=[N:40][CH:41]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

7

반응물 4

HCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 517044Potassium AcetateHCID 595482094-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineHCID 665999925-(Benzyloxy)-2-fluoropyridin-3-ylboronic acid

생성물 1

HCID 665999874-(5-(Benzyloxy)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine수율 41.8%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.150 g, 0.390 mmol), 5-(benzyloxy)-2-fluoropyridin-3-ylboronic acid (0.107 g, 0.432 mmol), Amphos (Aldrich) (0.014 g, 0.020 mmol), potassium acetate (Strem) (0.119 g, 1.22 mmol), EtOH (3 mL), and water (0.3 mL) was sealed under N2 and heated in a microwave at 100° C. for 20 min. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 10% to 20% EtOAc in hexanes) to give the product as a white solid (0.090 g). m/z (ESI, +ve ion) 552.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 8.17 (d, J=7.31 Hz, 1H); 8.01 (br. s., 1H); 7.31-7.48 (m, 5H); 7.23 (d, J=7.89 Hz, 4H); 6.87 (t, J=7.60 Hz, 4H); 5.13 (s, 2H); 4.81 (d, J=6.28 Hz, 3H); 3.81 (d, J=8.33 Hz, 6H); 2.55 (s, 3H).

후처리

  1. customwas sealed under N2
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (40 g, 10% to 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a8cec71d571d4ae78b3cd655a621962f
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772480B2

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