Hydrochloric Acid → N-(4-(3-(benzyloxy)phenoxy)pyridin-2-yl)-4-methylthiazol-2-amine

HRID 910968노트

반응식

HRID 910968 반응식
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3O)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].BrC[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>CCOCC.CN(C=O)C>[CH2:22]([O:25][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:13]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 24826061(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)phenol

생성물 1

HCID 24826501N-(4-(3-(benzyloxy)phenoxy)pyridin-2-yl)-4-methylthiazol-2-amine수율 38.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6228Dimethylformamide용매

실험 절차

A mixture (2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenol (0.150 g, 0.501-mmol), potassium carbonate (0.208 g, 1.50 mmol), 1-(bromomethyl)benzene (0.0857 g, 0.501 mmol), and DMF (2 mL) was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate was washed with water and brine, dried and concentrated. The residue was purified via MPLC (Biotage) eluting with 7:3 hexane:ethyl acetate to afford the free base. The free base was dissolved in ether (4 mL) and 1M HCl in ether (1 mL) was added. The mixture was diluted with hexanes (5 mL) and triturated. The solids were collected by filtration, washed with hexanes, and dried to afford the desired product (0.075 g, 35.1% yield) as a white powder. 1H NMR (d6-DMSO) δ 10.5 (bs, 1H), 8.24 (d, 1H), 7.33-7.47 (m, 6H), 6.98 (d, 1H), 6.90 (s, 1H), 6.80 (d, 1H), 6.58-6.60 (m, 3H), 5.13 (s, 2H), 2.25 (s, 3H).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe ethyl acetate was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with 7:3 hexane
  7. customethyl acetate to afford the free base
  8. customtriturated
  9. filtrationThe solids were collected by filtration
  10. washwashed with hexanes
  11. customdried

출처 및 근거

ORD 기록
ord-d089f5acecdd48bfb8e9b96a90e482bf
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022222B2

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