Hydrochloric Acid → HCID 178458934、化合物

HRID 2272667ノート

反応式

HRID 2272667 の反応式
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]3[N:16]=[C:15]([C:17]4[S:21][C:20]([C:22]([C@H:26]5[CH2:31][CH2:30][C@H:29]([C:32]([O:34]C)=[O:33])[CH2:28][CH2:27]5)([OH:25])[CH2:23][CH3:24])=[N:19][CH:18]=4)[CH:14]=[C:13]([CH3:36])[CH:12]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[K+].CO.Cl>O.C(O)(C)C.C(Cl)(Cl)Cl>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]3[N:16]=[C:15]([C:17]4[S:21][C:20]([C:22]([C@H:26]5[CH2:27][CH2:28][C@H:29]([C:32]([OH:34])=[O:33])[CH2:30][CH2:31]5)([OH:25])[CH2:23][CH3:24])=[N:19][CH:18]=4)[CH:14]=[C:13]([CH3:36])[CH:12]=3)[CH:5]=2)[CH2:2][CH2:3]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 178458935HCID 178458935、化合物

生成物 1

HCID 178458934HCID 178458934、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3776Isopropanol溶媒HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

To a flask containing methyl trans-4-[1-(5-{6-[(4-cyclopropylpyridin-2-yl)amino]-4-methylpyridin-2-yl}-1,3-thiazol-2-yl)-1-hydroxypropyl]-cyclohexanecarboxylate (198 mg, 0.391 mmol) and potassium hydroxide (88 mg, 1.563 mmol) was added methanol (1 mL) and water (1 mL). The reaction vessel was sealed and heated to 80° C. for a period of 14 hours. After cooling the reaction, aqueous hydrochloric acid (1.0 M, 1.56 mL, 1.56 mmol) was added. The cloudy solution was diluted with additional water (10 mL) and stirring was continued for one hour. Chloroform and isopropanol (4:1; 20 mL total) were added and the biphasic mixture was transferred to a separatory funnel. The organic phase was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to yield trans-4-[1-(5-{6-[(4-cyclopropylpyridin-2-yl)amino]-4-methylpyridin-2-yl}-1,3-thiazol-2-yl)-1-hydroxypropyl]cyclohexanecarboxylic acid. MS ESI calc'd. for C27H33N4O3S [M+H]+ 493. found 493. 1H NMR (500 MHz, DMSO-d6) δ 11.60-10.74 (br s, 1H), 8.48 (s, 1H), 8.27 (s, 1H), 7.75-7.29 (m, 2H), 7.26 (m, 2H), 5.68-5.47 (m, 1H), 2.42 (s, 3H), 2.29-2.12 (m, 1H), 2.12-1.84 (m, 7H), 1.84-1.73 (m, 1H), 1.54-1.42 (m, 1H), 1.43-1.13 (m, 6H), 1.13-0.97 (m, 3H), 0.88 (t, J=7.3 Hz, 3H). rhSyk activity=+++.

後処理

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. additionwas added
  4. customthe biphasic mixture was transferred to a separatory funnel
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-614a6bd8c68f42b08dc75808a3493917
出典データセット
uspto-grants-2015_09
特許番号
US09120785B2

反応ノート

読み込み中…