Hydrochloric Acid → 1-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(4-isopropyl-thiazol-2-yl)-quinazolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid

HRID 1443436ノート

反応式

HRID 1443436 の反応式
[CH2:1]([N:7]([CH3:27])[C:8]([CH:10]1[CH2:14][CH:13]([OH:15])[CH2:12][CH:11]1[C:16]([NH:18][C:19]1([C:24]([OH:26])=[O:25])[CH2:21][CH:20]1[CH:22]=[CH2:23])=[O:17])=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[H-].[Na+].Cl[C:31]1[C:40]2[C:35](=[CH:36][C:37](OC)=[CH:38][CH:39]=2)[N:34]=[C:33]([C:43]2[S:44][CH:45]=[C:46]([CH:48]([CH3:50])[CH3:49])[N:47]=2)[N:32]=1.Cl>C1COCC1.CCOC(C)=O>[CH2:1]([N:7]([CH3:27])[C:8]([CH:10]1[CH2:14][CH:13]([O:15][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[C:33]([C:43]3[S:44][CH:45]=[C:46]([CH:48]([CH3:50])[CH3:49])[N:47]=3)[N:32]=2)[CH2:12][CH:11]1[C:16]([NH:18][C:19]1([C:24]([OH:26])=[O:25])[CH2:21][CH:20]1[CH:22]=[CH2:23])=[O:17])=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 591654744-Chloro-7-methoxy-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinazolineHCID 668702741-{[2-(Hex-5-enylmethylcarbamoyl)-4-hydroxycyclopentanecarbonyl]amino}-2-vinylcyclopropanecarboxylic acid

生成物 1

HCID 684096781-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(4-isopropyl-thiazol-2-yl)-quinazolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid収率 78%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Compound 37 (26 mg, 70 μmol) was dissolved in THF (3 mL, dried with mol. siev.). To this solution was added NaH (60% in oil, 8.2 mg, 210 μmol) and the reaction was incubated for 10 min at ambient temperature. To the reaction mixture was then added compound 39 (17.6 mg, 61 μmol) followed by incubation at ambient temperature for 16 h. To the reaction was then added 0.1 M HCl (aq) and EtOAc, the phases separated and the aqueous phase extracted with another portion of EtOAc. The pooled organic phases were dried (MgSO4), filtered and concentrated in vacuo which gave a crude product which was further purified by flash-chromatography (Silica; DCM:MeOH) to afford the title compound (30 mg, 78%). LC/MS>95%, m/z (ESI+)=632 (MH+).

後処理

  1. customthe phases separated
  2. extractionthe aqueous phase extracted with another portion of EtOAc
  3. dry with materialThe pooled organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo which
  6. customgave a crude product which
  7. customwas further purified by flash-chromatography (Silica; DCM:MeOH)

出典と根拠

ORDレコード
ord-22035a8f7ec3439ab6fd235646400789
出典データセット
uspto-grants-2010_02
特許番号
US07659245B2

反応ノート

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