Hydrochloric Acid → Methyl 6-((1R,2S)-2-aminocyclohexylamino)-4-cyano-2-(3-(methylsulfonyl)phenylamino)nicotinate

HRID 711480노트

반응식

HRID 711480 반응식
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:25]=[C:24]([C:26]#[N:27])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:30]=2)[N:17]=1)=O)(C)(C)C.Cl>CC(O)=O>[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:25]=[C:24]([C:26]#[N:27])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:30]=2)[N:17]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 67238136Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(3-(methylsulfonyl)phenylamino)nicotinate

생성물 1

HCID 67237982Methyl 6-((1R,2S)-2-aminocyclohexylamino)-4-cyano-2-(3-(methylsulfonyl)phenylamino)nicotinate수율 85%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(3-(methylsulfonyl)phenylamino)nicotinate (178.3 mg, 0.328 mmol) in HOAc (4 mL) was added HCl (4 mL, 132 mmol). The mixture was stirred at RT for 4 h and then concentrated under reduced pressure. Water (15 mL) and 1M HCl (15 mL) were added to the concentrate and the aqueous layer was washed with EtOAc (10 mL). The washed aqueous layer was basified with saturated aqueous NaHCO3 (50 mL) and extracted with EtOAc (2×30 mL). The organic layers were combined, washed with saturated aq NaHCO3 (20 mL), water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a brown solid (123.2 mg, 85%). 1H-NMR (CDCl3) δ ppm 1.45-16.4 (m, 6H), 1.77-1.79 (m, 4H), 3.06 (s, 3H), 3.17-3.18 (m, 1H), 3.94 (s, 3H), 4.10-4.14 (m, 1H), 6.03-6.05 (m, 1H), 6.29 (s, 1H), 7.48-7.51 (m, 1H), 7.58-7.60 (m, 1H), 7.71-7.72 (m, 1H), 8.53 (s, 1H), 11.01 (s, 1H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionWater (15 mL) and 1M HCl (15 mL) were added to the
  3. concentrationconcentrate
  4. washthe aqueous layer was washed with EtOAc (10 mL)
  5. extractionextracted with EtOAc (2×30 mL)
  6. washwashed with saturated aq NaHCO3 (20 mL), water (20 mL) and brine (20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-acf2b494143540b5ae79f08f007d3e26
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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