(S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate → (S)-4-Amino-N-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216907노트

반응식

HRID 216907 반응식
[C:1]([C@@H:3]([NH:22][C:23]([C:25]1([NH:31]C(=O)OC(C)(C)C)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:31][C:25]1([C:23]([NH:22][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)=[O:24])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

참가 물질

3

반응물 1

HCID 59568561(S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

생성물 1

HCID 49783665(S)-4-Amino-N-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide수율 52.9%

시약·촉매·용매 1

HCID 284Formic Acid용매

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온도
50 °C

실험 절차

To (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (v(ii)), 920 mg) was added formic acid (3 mL) and the mixture heated to 50° C. for 30 min. The mixture was evaporated to dryness, dissolved in methanol (9 mL) and purified on reverse phase HPLC eluting with 25 to 95% methanol in 0.1% TFA on a Waters SunFire column. The material was converted to free base by evaporating the relevant fractions, dissolving in dichloromethane (20 mL) and shaking with saturated sodium bicarbonate solution (20 mL). The dichloromethane was dried and evaporated to afford the titled compound as a solid (397 mg).

후처리

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in methanol (9 mL)
  3. custompurified on reverse phase HPLC
  4. washeluting with 25 to 95% methanol in 0.1% TFA on a Waters SunFire column
  5. customby evaporating the relevant fractions
  6. dissolutiondissolving in dichloromethane (20 mL)
  7. dry with materialThe dichloromethane was dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-ec13180bea404d1b84a075428da64433
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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