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Trifluoroacetic acid → 7-[2-(2-Amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrile

HRID 1468995
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HRID 1468995 반응식
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:16]2[C:21]([C:22]#[N:23])=[CH:20][N:19]=[C:18]3[CH:24]=[CH:25][S:26][C:17]=23)=[CH:11][N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[NH2:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:16]2[C:21]([C:22]#[N:23])=[CH:20][N:19]=[C:18]3[CH:24]=[CH:25][S:26][C:17]=23)=[CH:11][N:12]=1
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참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 86640519{5-[2-(6-Cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

생성물 1

HCID 866405207-[2-(2-Amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrile수율 88.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of {5-[2-(6-cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (36.1 mg, 0.09 mmol) and trifluoroacetic acid (1 ml) in 4 ml of dichloromethane was stirred at room temperature for 16 hr. Dichloromethane was evaporated, and the residue obtained was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution, dried over MgSO4, filtered, and concentrated in vacuum to give a yellow crude product 24 mg. (89%). 1H NMR (300 MHz, CD3OD) δ 8.85 (s, 1H), 8.46 (d, J=5.4 Hz, 1H), 7.59 (d, J=5.7 Hz, 1H), 7.14 (s, 1H), 4.19 (t, J=7.2 Hz, 2H), 3.22 (t, J=7.2 Hz, 2H); LC-MS (ESI) m/z 302.0 (M+1).

후처리

  1. customDichloromethane was evaporated
  2. customthe residue obtained
  3. washwashed with aqueous sodium bicarbonate solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-ef74d435eb6149cd9cfc5815a60725df
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006252B2

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