3-Cyanophenylboronic acid → 3-(2'-Amino-1'-(cyclohexylmethyl)-5'-oxo-2-phenyl-1',5'-dihydrospiro[chroman-4,4'-imidazole]-6-yl)benzonitrile

HRID 1408593

반응식

HRID 1408593 반응식
[NH2:1][C:2]1[N:3]([CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.[C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)#[N:32]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]([CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:37]4[CH:38]=[C:33]([CH:34]=[CH:35][CH:36]=4)[C:31]#[N:32])[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1

참가 물질

6

반응물 2

HCID 27343253-Cyanophenylboronic acidHCID 584244092'-amino-6-bromo-1'-(cyclohexylmethyl)-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one

생성물 1

HCID 584247763-(2'-Amino-1'-(cyclohexylmethyl)-5'-oxo-2-phenyl-1',5'-dihydrospiro[chroman-4,4'-imidazole]-6-yl)benzonitrile수율 31%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 10796Cesium carbonate용매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

Pd(PPh3)2Cl2 (10 mg, 0.014 mmol) in a 10 mL tube under Ar was treated sequentially with 2′-amino-6-bromo-1′-(cyclohexylmethyl)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (30 mg, 0.064 mmol) in 1,4-dioxane (1.5 mL), Cs2CO3 (2 N, 0.5 mL) and 3-cyanophenylboronic acid (19 mg, 0.128 mmol). The mixture was heated at 120° C. under microwave reactor for 0.5 h. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC followed by preparative HPLC to give pure 3-(2′-amino-1′-(cyclohexylmethyl)-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (9.74 mg, 31%). 1H-NMR (MeOD): 1.02 (m, 5H), 1.62 (m, 6H), 2.03 (m, 1H), 2.24 (m, 1H), 3.30 (m, 1H), 3.44 (m, 1H), 5.91 (m, 1H), 6.97 (m, 1H), 7.16 (m, 1H), 7.25 (m, 1H), 7.35 (m, 3H), 7.46 (m, 2H), 7.56 (m, 1H), 7.71 (m, 2H)

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the residue, which
  3. customwas purified by preparative TLC

출처 및 근거

ORD 기록
ord-535c62aeaa2a4c89a8b67c05db504e1b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921359B2

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