Trifluoroacetic acid → N-[[(2S)-1-benzylpyrrolidin-2-yl]methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589982노트

반응식

HRID 589982 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14](C(OC(C)(C)C)=O)[S:15]([N:18]1[C:23]2([CH2:25][CH2:24]2)[CH2:22][N:21]([C:26]2[C:27]3[CH:34]=[CH:33][N:32](C(OC(C)(C)C)=O)[C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][S:15]([N:18]1[C:23]2([CH2:24][CH2:25]2)[CH2:22][N:21]([C:26]2[C:27]3[CH:34]=[CH:33][NH:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68296033tert-butyl 4-[8-[[(2S)-1-benzylpyrrolidin-2-yl]methyl-tert-butoxycarbonyl-sulfamoyl]-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate2회

생성물 1

HCID 57411876N-[[(2S)-1-benzylpyrrolidin-2-yl]methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-butyl 4-[8-[[(2S)-1-benzylpyrrolidin-2-yl]methyl-tert-butoxycarbonyl-sulfamoyl]-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate (Intermediate 48) (0.57 mmol) was dissolved in DCM (10 mL) and added TFA (1 mL). The reaction mixture was stirred at rt for 16 h, then added NaHCO3 (15 mL) and extracted with EtOAc (2×25 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using EtOAc and MeOH in heptane as eluent.

후처리

  1. extractionadded NaHCO3 (15 mL) and extracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica

출처 및 근거

ORD 기록
ord-75bd5104d5b142e58c413a13002aafd9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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