Hydrochloric Acid → 3-[6-(5-Phenyl-thiazol-2-ylamino)-pyridin-3-yl]-propan-1-ol

HRID 1355442노트

반응식

HRID 1355442 반응식
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([NH2:14])=[S:13])=[N:9][CH:10]=1.Br[CH:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17](OC)OC.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[C:22]1([C:16]2[S:13][C:12]([NH:11][C:8]3[N:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=3)=[N:14][CH:17]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11064658(1-Bromo-2,2-dimethoxyethyl)benzeneHCID 18506785[5-(3-Hydroxy-propyl)-pyridin-2-yl]-thiourea

생성물 1

HCID 185067863-[6-(5-Phenyl-thiazol-2-ylamino)-pyridin-3-yl]-propan-1-ol

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

[5-(3-Hydroxy-propyl)-pyridin-2-yl]-thiourea (7-4), 2.20 g (10.4 mmol) was stirred in 20 mL EtOH. (1-Bromo-2,2-dimethoxy-ethyl)-benzene (3.83 g, 15.6 mmol)was added, dissolved in 12 mL EtOH. The reaction was heated to reflux. After 30 min, 8 mL of concentrated HCl (aq) was added. After 7 h the reaction was cooled to RT, and diluted with water. Na2CO3 (s) was added to pH 9. The resulting precipitate was filtered, and washed with water. To solid was added ether, the mixture was sonicated and filtered, washing with ether. Afford the titled compound as a white solid. 1H NMR (CDCl3): δ8.74 (bs, 1H), 8.25 (d, 1H, J=2.2 Hz), 7.57 (dd, 2H, J=1.7, 9.0 Hz)7.49 (dd, 1H, J=2.4, 8.4 Hz), 7.38 (t, 2H, J=7.7 Hz), 6.83 (d, 1H, J=8.2 Hz), 3.71 (m, 2H), 2.70 (t, 2H, J=6.7 Hz), 1.89 (m, 2H). Mp 153-154° C. MS [M+H]+=312.2.

후처리

  1. temperatureThe reaction was heated to reflux
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. additionTo solid was added ether
  5. customthe mixture was sonicated
  6. filtrationfiltered
  7. washwashing with ether

출처 및 근거

ORD 기록
ord-2defe3aa492945c7b1928d17c55145a5
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586423B2

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