Water → (R)-1-(2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)ethane-1,2-diol

HRID 1511015

反応式

HRID 1511015 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Cl[CH2:21][C:22]([C@@H:24]1[CH2:28][O:27]C(C)(C)[O:25]1)=O.O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:5]([NH:8][C:9]2[S:10][CH:21]=[C:22]([C@@H:24]([OH:25])[CH2:28][OH:27])[N:11]=2)=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 866314851-(5-Bromo-3-(4-fluorophenoxy)pyridin-2-yl)thioureaHCID 86644148(S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone

生成物 1

HCID 59443719(R)-1-(2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)ethane-1,2-diol収率 7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To 1-(5-bromo-3-(4-fluorophenoxy)pyridin-2-yl)thiourea (0.5 g, 1.5 mmol) in ethanol (50 mL) was added (S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone (0.34 g, 1.9 mmol) and the reaction stirred at 80° C. for 1 hr. The reaction was poured into water (250 mL) and the filtered. The solid was triturated with ethyl acetate and methanol. The solid was suspended in ethyl acetate (500 mL) and washed with 1 N NaOH (500 mL). The organics were concentrated and the crude material was purified by chromatography using 3 to 10% MeOH/CH2Cl2 as eluent to give (R)-1-(2-(5-bromo-3-(4-fluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)ethane-1,2-diol (0.043 g, 0.10 mmol, 7%) (APCI POS 426, 428 M+H).

後処理

  1. customThe solid was triturated with ethyl acetate and methanol
  2. washwashed with 1 N NaOH (500 mL)
  3. concentrationThe organics were concentrated
  4. customthe crude material was purified by chromatography

出典と根拠

ORDレコード
ord-1217e26112b44a1287e0d53fb949bd7d
出典データセット
uspto-grants-2012_07
特許番号
US08212045B2

関連ノート

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