Hydrochloric Acid → HCID 178458934, 화합물

HRID 2272667노트

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HRID 2272667 반응식
[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

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 178458935HCID 178458935, 화합물

생성물 1

HCID 178458934HCID 178458934, 화합물

시약·촉매·용매 3

HCID 962Water용매2회HCID 3776Isopropanol용매HCID 6212Chloroform용매

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온도
80 °C

실험 절차

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=+++.

후처리

  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

출처 및 근거

ORD 기록
ord-614a6bd8c68f42b08dc75808a3493917
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120785B2

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