Ammonia → (S)-4-Amino-N-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216986노트

반응식

HRID 216986 반응식
[C:1]([C@@H:3]([NH:21][C:22]([C:24]1([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[NH:16][C:15]=3[CH:20]=2)=[CH:7][CH:6]=1)#[N:2].N>C(O)=O.O>[NH2:30][C:24]1([C:22]([NH:21][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:18][C:17](=[O:19])[NH:16][C:15]=4[CH:20]=3)=[CH:9][CH:10]=2)=[O:23])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 59568584(S)-tert-Butyl 4-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

생성물 1

HCID 59568558(S)-4-Amino-N-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 962Water용매

실험 절차

(S)-tert-Butyl 4-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 33, step (ii), 160 mg) was heated at 50° C. in formic acid (0.5 mL) for 10 min. The cooled solution was diluted with water (50 mL) and basified with ‘880’ ammonia and the resulting precipitate extracted into ethyl acetate (200 mL). The dried extract was concentrated to dryness and purified purified by reversed phase HPLC (using a SunFire column) eluting with methanol/0.1% aqueous trifluoroacetic acid. The pure fractions were freeze dried to afford the titled compound as a trifluoroacetatic acid salt (36 mg) TFA salt as a colourless solid.

후처리

  1. extractionthe resulting precipitate extracted into ethyl acetate (200 mL)
  2. extractionThe dried extract
  3. concentrationwas concentrated to dryness
  4. custompurified
  5. custompurified by reversed phase HPLC (
  6. washeluting with methanol/0.1% aqueous trifluoroacetic acid
  7. customdried

출처 및 근거

ORD 기록
ord-38eb457326b84c719fa57a4cba17d14b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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