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Hydrochloric Acid → (S)-5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(3-(methylamino)piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 1042651
ノート
印刷プレビュー

反応式

HRID 1042651 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([F:44])=[C:14]([CH:43]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][C@H:30]([N:34](C)[C:35](=O)OC(C)(C)C)[CH2:29]2)=[O:16])=[CH:4][N:3]=1.Cl.C(Cl)Cl.[OH-].[Na+]>O1CCOCC1.CCOC(C)=O.CO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([F:44])=[C:14]([CH:43]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][C@H:30]([NH:34][CH3:35])[CH2:29]2)=[O:16])=[CH:6][N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 16109030(S)-tert-butyl 1-(2-(5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluorobenzamido)-4-(trifluoromethyl)phenyl)piperidin-3-yl(methyl)carbamate

生成物 1

HCID 16109020(S)-5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(3-(methylamino)piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To a yellow solution of (S)-tert-butyl 1-(2-(5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluorobenzamido)-4-(trifluoromethyl)phenyl)piperidin-3-yl(methyl)carbamate (0.397 g, 0.65 mmol) in 3 mL dioxane at 0 deg. C was added hydrogen chloride 4.0 M in dioxane (1.6 ml, 6.5 mmol). The reaction was allowed to warm to ambient temp, as the clump, which formed would not go into solution. 3 mL of CH2Cl2, was added followed by 5 mL MeOH to give a homogenous yellow solution. After 30 min, the solution was concentrated in vacuo to give a yellow solid, which was treated with 1N NaOH and EtOAc. The organic layer was washed twice with 1N NaOH, dried over anhyd. Na2SO4, filtered, and concentrated in vacuo to give (S)-5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(3-(methylamino)piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide as a light yellow solid. MS m/z=513 [M+H]+. Calc'd for C26H24F4N6O: 512.

後処理

  1. customformed would not
  2. customto give a homogenous yellow solution
  3. concentrationthe solution was concentrated in vacuo
  4. customto give a yellow solid, which
  5. washThe organic layer was washed twice with 1N NaOH
  6. customdried over anhyd
  7. filtrationNa2SO4, filtered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5b349af3d0974c6aa105a64e318902b7
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08557996B2

反応ノート

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