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Diisopropylethylamine → N-(4-tert-butyl-6-morpholin-4-ylmethyl-pyridin-2-yl)-2-[2-fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetamide

HRID 1446765
ノート
印刷プレビュー

反応式

HRID 1446765 の反応式
Cl.Cl.[F:3][C:4]1[CH:9]=[C:8]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:25][C:26](O)=[O:27].[C:29]([C:33]1[CH:38]=[C:37]([CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:36]=[C:35]([NH2:46])[CH:34]=1)([CH3:32])([CH3:31])[CH3:30].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:29]([C:33]1[CH:38]=[C:37]([CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:36]=[C:35]([NH:46][C:26](=[O:27])[CH2:25][C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]4[CH:15]=[CH:16][C:17]([C:19]5[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=5)=[CH:18][C:13]4=[N:12][CH:11]=3)=[CH:9][C:4]=2[F:3])[CH:34]=1)([CH3:32])([CH3:30])[CH3:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68543260[2-Fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetic acid dihydrochlorideHCID 685448704-tert-Butyl-6-morpholin-4-ylmethyl-pyridin-2-ylamine

生成物 1

HCID 57863418
N-(4-tert-butyl-6-morpholin-4-ylmethyl-pyridin-2-yl)-2-[2-fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetamide
収率 64%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Dissolve [2-fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetic acid dihydrochloride (6.24 g, 14.84 mmol) and 4-tert-butyl-6-morpholin-4-ylmethyl-pyridin-2-ylamine (3.70 g, 14.84 mmol) in anhydrous DMF (40 mL). Add diisopropyl-ethylamine (8.5 mL, 48.97 mmol) and HATU (6.21 g, 16.32 mmol). Stir the reaction mixture at room temperature for 40 minutes. Dilute with ethyl acetate (800 mL). Wash with aqueous saturated sodium chloride (3×100 mL), sodium bicarbonate (sat. 3×100 mL), water (3×100 mL). Dry the organic layer over magnesium sulfate, filter off the drying reagent, and concentrate to oil. Chromatograph the crude product on silica (0-4% 2 M ammonia methanol/dichloro-methane). Recrystallize from dichloromethane/ether/hexane to provide the title compound 5.50 g (9.5 mmol, 64%) white solid as product. MS (ES), m/z 579 (M+1).

後処理

  1. washWash with aqueous saturated sodium chloride (3×100 mL), sodium bicarbonate (sat. 3×100 mL), water (3×100 mL)
  2. dry with materialDry the organic layer over magnesium sulfate
  3. filtrationfilter off the drying reagent
  4. concentrationconcentrate to oil
  5. customRecrystallize from dichloromethane/ether/hexane

出典と根拠

ORDレコード
ord-d6b13e6d309e42a8bee7af147b6f1603
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07666879B2

反応ノート

読み込み中…

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