2-Mercaptobenzoic Acid → N-(2-{2-Methyl-4-[((S)-phenyl-(S)-piperidin-2-yl-methyl)-amino]-quinolin-8-yloxy}-ethyl)methanesulfonamide dihydrochloride

HRID 1966526노트

반응식

HRID 1966526 반응식
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[C@@H:40]([NH:47][C:48]1[C:57]2[C:52](=[C:53]([O:58][CH2:59][CH2:60][NH:61][S:62]([CH3:65])(=[O:64])=[O:63])[CH:54]=[CH:55][CH:56]=2)[N:51]=[C:50]([CH3:66])[CH:49]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)C=C.SC1C=CC=CC=1C(O)=O.[OH-].[Na+].C(O)(C)C.O.[ClH:84]>C1COCC1>[ClH:84].[ClH:84].[CH3:66][C:50]1[CH:49]=[C:48]([NH:47][C@@H:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C@@H:35]2[CH2:36][CH2:37][CH2:38][CH2:39][NH:34]2)[C:57]2[C:52](=[C:53]([O:58][CH2:59][CH2:60][NH:61][S:62]([CH3:65])(=[O:63])=[O:64])[CH:54]=[CH:55][CH:56]=2)[N:51]=1

참가 물질

7

반응물 5

HCID 54432-Mercaptobenzoic AcidHCID 14798Sodium HydroxideHCID 821241,4-Bis(diphenylphosphino)butaneHCID 21409480Isopropanol-hcl-waterHCID 59474734N-[2-(4-{[(S)-((S)-1-Allylpiperidin-2-yl)-phenylmethyl]-amino}-2-methylquinolin-8-yloxy)ethyl]methanesulfonamide

생성물 1

HCID 68498582N-(2-{2-Methyl-4-[((S)-phenyl-(S)-piperidin-2-yl-methyl)-amino]-quinolin-8-yloxy}-ethyl)methanesulfonamide dihydrochloride수율 30%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Tris-(dibenzylidenaceton)-dipalladium(0) (19.0 mg, 0.021 mmole) and 1,4-bis(diphenylphosphino)butane (9 mg, 0.021 mmole) were mixed with THF (10 mL). N-[2-(4-{[(S)—((S)-1-Allylpiperidin-2-yl)-phenylmethyl]-amino}-2-methylquinolin-8-yloxy)-ethyl]-methanesulfonamide (example 35, 130 mg, 0.256 mmole) in THF (5 mL) and 2-mercaptobenzoic acid (86.7 mg, 0.562 mmole) in THF (5 mL) were added and the mixture was stirred at RT for 2 hrs. The content of the flask was mixed with 1N NaOH and extracted with dichloromethane. The organic layer was washed with water and saturated NaCl solution and concentrated. The residue thus obtained was cystallized from isopropanol/water/HCl to obtain a white solid (42 mg, 30%).

후처리

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and saturated NaCl solution
  3. concentrationconcentrated
  4. customThe residue thus obtained

출처 및 근거

ORD 기록
ord-69cc82f3695b4a3b8d63c256525f999d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420670B2

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