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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
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HRID 1042651 반응식
[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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b349af3d0974c6aa105a64e318902b7
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08557996B2

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