Dimethyl Sulfoxide → HCID 178472675、化合物

HRID 1047245ノート

反応式

HRID 1047245 の反応式
Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:16][O:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C>[Br:8][C:6]1[N:7]=[C:2]([NH:24][C@H:21]2[CH2:22][CH2:23][C@H:18]([O:17][CH3:16])[CH2:19][CH2:20]2)[C:3]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:4][CH:5]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetateHCID 178496609HCID 178496609、化合物

生成物 1

HCID 178472675HCID 178472675、化合物収率 45.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 6.B) (30.0 g, 88 mmol), trans-4-methoxycyclohexanamine (17.15 g, 133 mmol), N,N-diisopropylethylamine (30.8 mL, 177 mmol) and dimethylsulfoxide (70.8 mL) were combined in a reaction vial with a stirbar and heated in an oil bath at 150° C. for 16 h with stirring. The resulting mixture was diluted with ethyl acetate and the volatiles removed under reduced pressure. The residue was purified using silica gel chromatography on a Biotage SP1 (12% ethyl acetate in hexanes). Fractions containing the desired product were combined and organic volatiles removed under reduced pressure. The residue was triturated with 5% ethyl acetate in hexane. Solids were collected by vacuum filtration, washed with hexane and dried under vacuum to afford ethyl the title compound (15.37 g, 39.7 mmol, 44.8% yield) as an off-white solid. MS (ESI) m/z 387.0 [M]+, 389.0 [M+2]+.

後処理

  1. customthe volatiles removed under reduced pressure
  2. customThe residue was purified
  3. additionFractions containing the desired product
  4. customorganic volatiles removed under reduced pressure
  5. customThe residue was triturated with 5% ethyl acetate in hexane
  6. filtrationSolids were collected by vacuum filtration
  7. washwashed with hexane
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-a8e6eb14fcdb4c4a828c841805dff6f2
出典データセット
uspto-grants-2013_10
特許番号
US08569494B2

反応ノート

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