Triphenylphosphine → (R)-4-((R)-1-(6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

HRID 2209006ノート

反応式

HRID 2209006 の反応式
[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]3[N:17]([CH:20]([F:22])[F:21])[CH:18]=[N:19][C:12]=3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].O[C@H:24]([C@H:26]1[CH2:30][N:29]([C@@H:31]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[CH3:32])[C:28](=[O:41])[CH2:27]1)[CH3:25].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(Cl)Cl>[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([O:16][C@@H:24]([C@H:26]3[CH2:30][N:29]([C@@H:31]([C:33]4[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)[CH3:32])[C:28](=[O:41])[CH2:27]3)[CH3:25])[C:13]3[N:17]([CH:20]([F:21])[F:22])[CH:18]=[N:19][C:12]=3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71238294(4R)-4-[(1S)-1-hydroxyethyl]-1-[(1R)-1-(4-methoxyphenyl)ethyl]pyrrolidin-2-oneHCID 1178428876-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one

生成物 1

HCID 117843539(R)-4-((R)-1-(6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one 2.33 (33 mg, 0.107 mmol), lactam alcohol 1.05 (42 mg, 0.16 mmol), and PPh3 (44 mg, 0.17 mmol) were taken up in THF (1 mL). To the resulting suspension was added DEAD (26 μL, 0.17 mmol) dropwise. The resulting cloudy solution was heated to 40° C. and stirred 1.25 h. The solution was then diluted with DCM and concentrated directly onto silica gel. Purification by silica gel chromatography (15% to 60% acetone in hexanes) afforded (R)-4-((R)-1-(6-(1-tert-butyl-1H-pyrazol-4-yl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 2.34 that was used without further purification.

後処理

  1. concentrationconcentrated directly onto silica gel
  2. customPurification by silica gel chromatography (15% to 60% acetone in hexanes)

出典と根拠

ORDレコード
ord-f46f09b5625a492a95b6d759b71c1498
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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