Ammonium Hydroxide → 5-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 512494

반응식

HRID 512494 반응식
[Br:1][C:2]1[C:3](=[O:21])[C:4]([C:18]([OH:20])=O)=[CH:5][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[C:7]=1[CH3:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[CH3:54][S:55]([C:58]1[CH:65]=[CH:64][C:61]([CH2:62][NH2:63])=[CH:60][CH:59]=1)(=[O:57])=[O:56].[NH4+].[OH-]>CN(C=O)C.CO>[CH3:54][S:55]([C:58]1[CH:65]=[CH:64][C:61]([CH2:62][NH:63][C:18]([C:4]2[C:3](=[O:21])[C:2]([Br:1])=[C:7]([CH3:8])[N:6]([CH2:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=3)[CH:5]=2)=[O:20])=[CH:60][CH:59]=1)(=[O:56])=[O:57]

참가 물질

8

반응물 5

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867115285-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

생성물 1

HCID 867115365-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 1c, 1.00 g, 2.88 mmol), TBTU (0.925 g, 2.88 mmol), DIPEA (1.50 mL, 8.67 mmol) in DMF (7 mL) is stirred for 30 min. Then, 4-(methylsulfonyl)benzylamine hydrochloride (0.766 g, 3.46 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is diluted with MeOH, basified with NH4OH, filtered and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 0.66 g (29% of theory); ESI mass spectrum: [M+H]+=514 (bromine isotope pattern); Retention time HPLC: 0.88 min (Z003—001).

후처리

  1. filtrationfiltered
  2. custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
  3. custom0.88 min (Z003—001)

출처 및 근거

ORD 기록
ord-c0794c0ca32f45fcba4356828349a91d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102624B2

연결된 노트

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