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

HRID 1966526ノート

反応式

HRID 1966526 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-69cc82f3695b4a3b8d63c256525f999d
出典データセット
uspto-grants-2013_04
特許番号
US08420670B2

反応ノート

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