Toluene → tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-3-yloxy)ethyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 718612

反応式

HRID 718612 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]2[C:11]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:10][CH:9]=[N:8][N:7]2[C:18]=1[C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[N:23][CH:24]=1.O[C:39]1[CH:40]=[N:41][C:42]2[C:47]([CH:48]=1)=[CH:46][CH:45]=[CH:44][CH:43]=2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[O:15]1[CH2:16][CH2:17][N:12]([C:11]2[C:6]3[N:7]([C:18]([C:19]4[CH:20]=[CH:21][C:22]([N:25]5[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]5)=[N:23][CH:24]=4)=[C:4]([CH2:3][CH2:2][O:1][C:39]4[CH:40]=[N:41][C:42]5[C:47]([CH:48]=4)=[CH:46][CH:45]=[CH:44][CH:43]=5)[N:5]=3)[N:8]=[CH:9][CH:10]=2)[CH2:13][CH2:14]1

参加物

7

反応物 5

HCID 1140TolueneHCID 113763-HydroxyquinolineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 117732481tert-Butyl 4-(5-(2-(2-hydroxyethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 117732482tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-3-yloxy)ethyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Compound 28f (97.3 mg, 0.191 mmol), 3-hydroxyquinoline (38.8 mg, 0.267 mmol), and PPh3 (70.1 mg, 0.267 mmol) were placed in an 8 mL vial equipped with a stir bar. DCM (2 mL) was added and the mixture was stirred at rt for 5 min. 40% Diethyl azodicarboxylate in toluene (0.104 mL, 0.229 mmol) was added dropwise and then the resulting solution was stirred at rt for 30 min. The crude reaction was chromatographed on a 12 g SiO2 pre-packed column and eluted with 0-80% ACN/DCM to afford compound 28g. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.59 (d, J=2.9 Hz, 1H), 8.47 (d, J=2.2 Hz, 1H), 7.95-8.05 (m, 2H), 7.84 (dd, J=8.8, 2.2 Hz, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.45-7.59 (m, 2H), 7.37 (d, J=2.7 Hz, 1H), 6.77 (d, J=8.8 Hz, 1H), 6.07 (d, J=5.6 Hz, 1H), 4.51 (t, J=6.7 Hz, 2H), 3.87-4.00 (m, 8H), 3.52-3.65 (m, 8H), 3.38 (t, J=6.7 Hz, 2H), 1.50 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C35H40N8O4: 637.3 (M+H). Found: 637.3.

後処理

  1. customvial equipped with a stir bar
  2. stirringthe resulting solution was stirred at rt for 30 min
  3. customThe crude reaction
  4. customwas chromatographed on a 12 g SiO2 pre-packed column
  5. washeluted with 0-80% ACN/DCM

出典と根拠

ORDレコード
ord-659efebac53f446caf1b8d87525f450a
出典データセット
uspto-grants-2015_11
特許番号
US09193736B2

関連ノート

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