Diisopropylethylamine → (E)-N-{(S)-2-[4-(4-Fluoro-benzoyl)-piperidin-1-yl]-1-hydroxymethyl-ethyl)-3-(5-cyano-2-methoxy-phenyl)-acrylamide

HRID 434304

반응식

HRID 434304 반응식
Cl.[NH2:2][C@H:3]([CH2:20][OH:21])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])[CH2:7][CH2:6]1.C(N(C(C)C)CC)(C)C.[C:31]([C:33]1[CH:34]=[CH:35][C:36]([O:44][CH3:45])=[C:37](/[CH:39]=[CH:40]/[C:41](O)=[O:42])[CH:38]=1)#[N:32].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>ClCCl>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([CH:8]2[CH2:7][CH2:6][N:5]([CH2:4][C@H:3]([NH:2][C:41](=[O:42])/[CH:40]=[CH:39]/[C:37]3[CH:38]=[C:33]([C:31]#[N:32])[CH:34]=[CH:35][C:36]=3[O:44][CH3:45])[CH2:20][OH:21])[CH2:10][CH2:9]2)=[O:12])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11458357(E)-3-(5-cyano-2-methoxy-phenyl)-acrylic acidHCID 68809497[1-((S)-2-Amino-3-hydroxy-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanone hydrochloride

생성물 1

HCID 69986033(E)-N-{(S)-2-[4-(4-Fluoro-benzoyl)-piperidin-1-yl]-1-hydroxymethyl-ethyl)-3-(5-cyano-2-methoxy-phenyl)-acrylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of [1-((S)-2-amino-3-hydroxy-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanone hydrochloride (1.8 g, 5.7 mmol) and diisopropylethylamine (2.0 ml, 11.4 mmol) in dichloromethane (45 ml) is added (E)-3-(5-cyano-2-methoxy-phenyl)-acrylic acid (1.1 g, 5.7 mmol) followed by 2-(1H benzotriazol-1-yl)-1,1,3,3,-tetramethyluronium tetrafluoroborate (1.83 g, 5.7 mmol). The reaction mixture is stirred at ambient temperature for 4.5 hours, then filtered and the filtrate washed with water (50 ml), saturated sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml). The organic phase is dried over magnesium sulphate, the solvent evaporated and the residue purified by flash silica chromatography (dichloromethane:methanol; 98:2 to 92:8 elution gradient) to afford the product, [MH]+466.1.

후처리

  1. filtrationfiltered
  2. washthe filtrate washed with water (50 ml), saturated sodium bicarbonate solution (50 ml), water (50 ml) and brine (50 ml)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customthe solvent evaporated
  5. customthe residue purified by flash silica chromatography (dichloromethane:methanol; 98:2 to 92:8 elution gradient)
  6. customto afford the product, [MH]+466.1

출처 및 근거

ORD 기록
ord-027795b7f3a748158af9e2b8b8b6ecbc
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670379B2

연결된 노트

불러오는 중…