Trifluoroacetic acid → 6-(5-((S)-2-amino-3-(4(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one

HRID 2075340노트

반응식

HRID 2075340 반응식
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3[S:15][C:14]([N:16](C(OC(C)(C)C)=O)[CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[N:13][N:12]=3)=[CH:10][C:4]=2[O:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=1)[CH2:17][NH:16][C:14]1[S:15][C:11]([C:9]2[CH:8]=[CH:7][C:5]3[NH:6][C:2](=[O:1])[O:3][C:4]=3[CH:10]=2)=[N:12][N:13]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 57991881tert-Butyl (S)-1-(5-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

생성물 1

HCID 579918766-(5-((S)-2-amino-3-(4(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one수율 53%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl (S)-1-(5-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (130 mg, 205 μmol) in 10 mL DCM was treated with 10 mL TFA for 60 minutes. After removing the solvent, the remaining residue was dissolved in 100 mL EtOAc. The resulting solution was washed with a mixture of aqueous saturated sodium bicarbonate plus 5% 5N NaOH, then twice with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate. Removal of the solvent gave the title compound 6-(5-((S)-2-amino-3-(4(trifluoromethyl)phenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one as an off-white amorphous solid (47 mgs, 53%). LCMS (API-ES) m/z (%): 436.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 2.78 (dd, J=13.60, 7.53 Hz, 1H) 2.99 (dd, J=13.60, 5.58 Hz, 1H) 3.35-3.40 (m, 1H) 3.40-3.47 (m, 1H) 3.48-3.55 (m, 1H) 7.13 (d, J=8.22 Hz, 1H) 7.48 (d, J=8.02 Hz, 2H) 7.53 (dd, J=8.12, 1.47 Hz, 1H) 7.62 (d, J=7.24 Hz, 3H).

후처리

  1. customAfter removing the solvent
  2. dissolutionthe remaining residue was dissolved in 100 mL EtOAc
  3. washThe resulting solution was washed with a mixture of aqueous saturated sodium bicarbonate plus 5% 5N NaOH
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-c814139a932742238042a6288f4db035
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919504B2

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