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Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

HRID 879381
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HRID 879381 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:27]=[C:26]4[C:22]([C:23](=[O:30])[N:24]([CH3:29])[N:25]4[CH3:28])=[CH:21][CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:27]=[C:26]4[C:22]([C:23](=[O:30])[N:24]([CH3:29])[N:25]4[CH3:28])=[CH:21][CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 86700190(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

생성물 1

HCID 72195837(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

To a stirred solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-3-oxo-2,3-dihydro-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (27.2 mg, 0.047 mmol) in THF (1.0 mL) and methanol (1.0 mL) was added 1N NaOH solution (0.5 mL, excess). The reaction mixture was stirred at 50° C. for 2 h and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C29H29ClN3O4S: 550.2; found: 550.2. 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.96 (s, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.93 (dd, J=8.0, 0.8 Hz, 2H), 7.55-7.49 (m, 3H), 5.33 (s, 1H), 3.50 (s, 3H), 3.39 (s, 3H), 2.60 (s, 3H), 1.01 (s, 9H).

후처리

  1. custompurified by reverse phase HPLC
  2. washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

출처 및 근거

ORD 기록
ord-455e79f7ff9f47f4bc34e431b7c42f77
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987250B2

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