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

HRID 516016ノート

反応式

HRID 516016 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-942428e5023b456db239824b66c5f3da
出典データセット
uspto-grants-2015_08
特許番号
US09108970B2

反応ノート

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