Hydrochloric Acid → HCID 59415756、化合物

HRID 2061881ノート

反応式

HRID 2061881 の反応式
[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:11]=[CH:10][C:9](B(O)O)=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)[CH:7]=1)[CH3:2].C(NC(NC1C=C(C2SC=C(C(F)(F)F)N=2)C(B2OC(C)(C)C(C)(C)O2)=CN=1)=O)C.[F:55][C:56]1[CH:64]=[CH:63][C:62](I)=[CH:61][C:57]=1[C:58]([OH:60])=[O:59].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O1CCOCC1.O.CCOC(C)=O>[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:62]2[CH:63]=[CH:64][C:56]([F:55])=[C:57]([CH:61]=2)[C:58]([OH:60])=[O:59])=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)[CH:7]=1)[CH3:2]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 27789252-Fluoro-5-iodobenzoic acidHCID 592084681-Ethyl-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-yl)urea2 回HCID 594161896-(3-Ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid

生成物 1

HCID 59415756HCID 59415756、化合物収率 60.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
0 °C

実験手順

6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 17, 0.261 g, 0.72 mmol, Intermediate 17) and 2-fluoro-5-iodobenzoic acid (0.175 g, 0.66 mmol, aldrich) were combined in dioxane (1 ml). A solution of cesium carbonate (0.364 g, 1.12 mmol) in water (0.658 ml) was added followed by tetrakis(triphenylphosine)palladium(0) (0.076 g, 0.07 mmol, strem) and additional dioxane (2.63 ml). The flask was placed in an oil bath preheated to 100° C. and was heated for 1h., then cooled to 0° C. and 1 N HCl was added until the pH was ˜3. EtOAc (5 ml) was added and a solid crashed out and was collected by filtration and washed with EtOAc, then dried to give a grey solid 5-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-2-fluorobenzoic acid (0.180 g, 60.2%).

後処理

  1. customThe flask was placed in an oil bath
  2. custompreheated to 100° C.
  3. temperaturewas heated for 1h.
  4. filtrationwas collected by filtration
  5. washwashed with EtOAc
  6. customdried

出典と根拠

ORDレコード
ord-4264cf7a6a7e42d8ace2a649e5339d9d
出典データセット
uspto-grants-2012_10
特許番号
US08283361B2

反応ノート

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