Acetonitrile--water (1/1) → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-6-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 510286노트

반응식

HRID 510286 반응식
[C:1]([O:5][C@@H:6]([C:9]1[C:27]([CH3:28])=[CH:26][C:12]2[N:13]=[C:14]([C:16]3[CH:17]=[C:18]4[N:24]([CH3:25])[N:23]=[CH:22][C:19]4=[N:20][CH:21]=3)[S:15][C:11]=2[C:10]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[CH2:7][OH:8])([CH3:4])([CH3:3])[CH3:2].C(#N)C.[OH2:39]>>[C:1]([O:5][C@@H:6]([C:9]1[C:27]([CH3:28])=[CH:26][C:12]2[N:13]=[C:14]([C:16]3[CH:17]=[C:18]4[N:24]([CH3:25])[N:23]=[CH:22][C:19]4=[N:20][CH:21]=3)[S:15][C:11]=2[C:10]=1[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:7]([OH:39])=[O:8])([CH3:4])([CH3:2])[CH3:3]

참가 물질

3

반응물 2

HCID 18373917Acetonitrile--water (1/1)HCID 86699817(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-6-yl)benzo[d]thiazol-6-yl)ethanol

생성물 1

HCID 72195157(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-6-yl)benzo[d]thiazol-6-yl)acetic acid

실험 절차

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-6-yl)benzo[d]thiazol-6-yl)ethanol (50 mg, 0.099 mmol) in acetonitrile/water (2 mL/0.5 mL) was added CrO3/H5IO6 (0.439M, 1.1 mL, 0.483 mmol) and CrO3 (20 mg, 0.198 mmol). The reaction solution was stirred at room temperature for 1 h and quenched with 5% Na2S2O3 solution. The mixture was extracted with ethyl acetate, washed with water and brine. The organic solution was dried and concentrated to give crude which was purified by reverse phase HPLC, eluting by 5-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+: calc'd for C27H25ClN4O3S: 521.14 (M+H+); Found: 521.2 (M+H+), 1H NMR (400 MHz, CD3OD) δ 9.20 (d, J=8 Hz, 1H), 8.67 (s, 1H), 8.24 (s, 1H), 7.88 (s, 1H), 7.71-7.59 (m, 4H), 5.27 (s, 1H), 4.16 (s, 3H), 2.62 (s, 3H), 0.98 (s, 9H).

후처리

  1. customquenched with 5% Na2S2O3 solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. customThe organic solution was dried
  5. concentrationconcentrated
  6. customto give crude which
  7. customwas purified by reverse phase HPLC
  8. washeluting by 5-100% acetonitrile in H2O with 0.1% TFA

출처 및 근거

ORD 기록
ord-b75c170ecd20457789ac8f3560dad65a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096586B2

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