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Hydrochloric Acid → 2-[1-(2,1,3-Benzoxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)pyrrolo[2,3-c]pyridin-5-yl]-2-tert-butoxy-acetic acid

HRID 1473211
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HRID 1473211 반응식
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[C:15]4[C:16](=[O:38])[N:17]([CH3:37])[C:18]([CH:27]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:28]([O:30]C)=[O:29])=[C:19]([C:20]5[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=5)[C:14]=4[CH:13]=[CH:12]3)[CH:7]=[CH:6][C:5]=12.[Li+].[OH-].Cl>O1CCCC1.CO>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH2:10][N:11]3[C:15]4[C:16](=[O:38])[N:17]([CH3:37])[C:18]([CH:27]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[C:28]([OH:30])=[O:29])=[C:19]([C:20]5[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=5)[C:14]=4[CH:13]=[CH:12]3)[CH:7]=[CH:6][C:5]=12
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89473336methyl 2-(1-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate

생성물 1

HCID 715387522-[1-(2,1,3-Benzoxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)pyrrolo[2,3-c]pyridin-5-yl]-2-tert-butoxy-acetic acid

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A mixture of the crude methyl 2-(1-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate in Tetrahydrofuran (THF) (1 mL) and Methanol (1 mL) was treated with 2M LiOH (1 mL, 2.000 mmol) and then heated to 70° C. for one hour. The mixture was cooled to 0° C., adjusted to pH <2 with 1N HCl and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min.) to give the title compound. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.77-7.85 (m, 1H) 7.52-7.59 (m, 1H) 7.41-7.49 (m, 2H) 7.36-7.41 (m, 1H) 7.29-7.34 (m, 2H) 7.05-7.13 (m, 1H) 6.09-6.19 (m, 1H) 5.87-6.02 (m, 2H) 5.46-5.52 (m, 1H) 3.66 (s, 3H) 2.45 (s, 3H) 1.00 (s, 9H); LCMS (m/z) ES+=501 (M+1).

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min.)

출처 및 근거

ORD 기록
ord-b6a0ca1962a04bcf941dfac2632ec0f7
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09012642B2

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