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2-Methoxyethyl chloroformate → 2-Methoxyethyl 4-[4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)pyrazol-1-yl]piperidine-1-carboxylate

HRID 908463
ノート
印刷プレビュー

反応式

HRID 908463 の反応式
Cl[C:2]([O:4][CH2:5][CH2:6][O:7][CH3:8])=[O:3].[O:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]1[C:18]1[C:19]([NH2:35])=[N:20][CH:21]=[C:22]([C:24]2[CH:25]=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:28]=2)[CH:23]=1>N1C=CC=CC=1>[NH2:35][C:19]1[N:20]=[CH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]([CH:29]3[CH2:34][CH2:33][N:32]([C:2]([O:4][CH2:5][CH2:6][O:7][CH3:8])=[O:3])[CH2:31][CH2:30]3)[CH:28]=2)=[CH:23][C:18]=1[C:10]1[O:9][C:17]2[C:12]([N:11]=1)=[N:13][CH:14]=[CH:15][CH:16]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 694002-Methoxyethyl chloroformateHCID 576870643-Oxazolo[4,5-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

生成物 1

HCID 576870822-Methoxyethyl 4-[4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)pyrazol-1-yl]piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
25 °C

実験手順

2-methoxyethyl chloroformate (0.035 ml) at 25° C. was added over a period of 5 minutes under argon to a stirred mixture of 3-oxazolo[4,5-b]pyridin-2-yl-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (90 mg) and pyridine (5 ml). The resulting suspension was stirred at 25° C. for 2 hours. The solvent was evaporated. A solution of ammonia in methanol 7N (1 ml) was added and the mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 2-methoxyethyl 4-[4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)pyrazol-1-yl]piperidine-1-carboxylate (75 mg) as a solid. NMR Spectrum: (CDCl3): 1.95-2.07 (m, 2H), 2.17-2.26 (m, 2H), 3.01 (bs, 2H), 3.40 (s, 3H), 3.63 (t, 2H), 4.28 (bs, 2H), 4.29-4.44 (m, 3H), 7.02 (bs, 2H), 7.35 (dd, 1H), 7.69 (s, 1H), 7.79 (s, 1H), 7.90 (dd, 1H), 8.41 (d, 1H), 8.42 (d, 1H), 8.59 (dd, 1H); Mass spectrum: M+H+ 464.

後処理

  1. customThe solvent was evaporated
  2. additionA solution of ammonia in methanol 7N (1 ml) was added
  3. customThe crude product was purified by flash chromatography on silica gel eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane
  4. customThe solvent was evaporated to dryness

出典と根拠

ORDレコード
ord-8e3483e6c25d4918b81fd625cd381d6b
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017611B2

反応ノート

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