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

HRID 1355442ノート

反応式

HRID 1355442 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-2defe3aa492945c7b1928d17c55145a5
出典データセット
uspto-grants-2003_07
特許番号
US06586423B2

反応ノート

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