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Hydrochloric Acid → 2-(5-(4-(6-Fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

HRID 1024446
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HRID 1024446 반응식
[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[S:20][C:19]([C:21]([NH:23][CH:24]([CH:30]([CH3:32])[CH3:31])[C:25]([O:27]CC)=[O:26])=[O:22])=[N:18][CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[S:20][C:19]([C:21]([NH:23][CH:24]([CH:30]([CH3:32])[CH3:31])[C:25]([OH:27])=[O:26])=[O:22])=[N:18][CH:17]=4)=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 52934820Ethyl 2-(5-(4-(6-fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate

생성물 1

HCID 529348192-(5-(4-(6-Fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

To a solution of Ethyl 2-(5-(4-(6-fluorobenzo[d]thiazol-2-ylamino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 19, 80 mg) in THF (1.6 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (0.32 ml) and the mixture was stirred at RT for 4 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get yellow solid, which was crystallized in ethyl acetate to give the title compound. Yield: 58 mg (77%); 1HNMR (DMSO-d6, 300 MHz): δ 12.99 (bs, 1H), 10.76 (s, 1H), 8.36 (s, 1H), 8.34 (d, 1H), 7.88 (d, 2H), 7.8 (d, 2H), 7.77 (d, 1H), 7.65 (dd, 1H), 7.2 (m, 1H), 4.32, (m, 1H), 2.27 (m, 1H), 0.97 (d, 6H); MS (ES+): m/z 471 (M+1).

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get yellow solid, which
  6. customwas crystallized in ethyl acetate

출처 및 근거

ORD 기록
ord-053b8fccc1f445bb8793961b35bae020
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722901B2

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