Triethylamine → (3-((3-(3,6-Dihydro-2H-pyran-4-YL)pyridin-2-YL)oxy)azetidin-1-YL)(pyrimidin-4-YL)methanone

HRID 2207848ノート

反応式

HRID 2207848 の反応式
Cl.[NH:2]1[CH2:5][CH:4]([O:6][C:7]2[C:12]([C:13]3[CH2:14][CH2:15][O:16][CH2:17][CH:18]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:3]1.[N:19]1[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[N:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:16]1[CH2:15][CH:14]=[C:13]([C:12]2[C:7]([O:6][CH:4]3[CH2:3][N:2]([C:25]([C:22]4[CH:23]=[CH:24][N:19]=[CH:20][N:21]=4)=[O:26])[CH2:5]3)=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:18][CH2:17]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 1693064-Pyrimidinecarboxylic acidHCID 674774502-(Azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-YL)pyridine hydrochloride

生成物 1

HCID 58547745(3-((3-(3,6-Dihydro-2H-pyran-4-YL)pyridin-2-YL)oxy)azetidin-1-YL)(pyrimidin-4-YL)methanone収率 66%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(azetidin-3-yloxy)-3-(3,6-dihydro-2H-pyran-4-yl)pyridine hydrochloride (see PREPARATION P26.1; 100 mg, 0.45 mmol), pyrimidine-4-carboxylic acid (55 mg, 0.45 mmol) and triethylamine (96.13 mg, 0.95 mmol) in CH2Cl2 (10 mL) was added 4-Dimethylaminopyridine (DMAP) (55 mg, 0.47 mmol) and propyl phosphonic anhydride (500 mg, 0.9 mmol). The reaction mixture was stirred at room temperature for overnight. Then the reaction mixture was concentrated and the crude product was purified by silica gel column chromatography to give the desired compound (48 mg, 0.16 mmol, yield 66%). [M+1]: 339. IC50 (uM): 0.99.

後処理

  1. concentrationThen the reaction mixture was concentrated
  2. customthe crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-302a20444cd74767a1c4bfcedc7c9482
出典データセット
uspto-grants-2016_06
特許番号
US09376450B2

反応ノート

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