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Hydrochloric Acid → 2-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylic acid

HRID 1928618
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인쇄 미리보기

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HRID 1928618 반응식
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]5[N:30]=[CH:29][C:28]([C:31]([O-:33])=[O:32])=[CH:27][N:26]=5)[CH2:21][CH2:20]4)[N:15]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Na+].Cl>CO>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH:19]4[CH2:20][CH2:21][N:22]([C:25]5[N:26]=[CH:27][C:28]([C:31]([OH:33])=[O:32])=[CH:29][N:30]=5)[CH2:23][CH2:24]4)[N:15]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866306322-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylate

생성물 1

HCID 577083752-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylic acid

시약·촉매·용매 1

HCID 887
Methanol
용매

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온도
60 °C

실험 절차

Ethyl 4-(2-(4-(4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)pyrimidine-5-carboxylate (0.8 g, 0.00167 mol) (Example 60) was dissolved in MeOH (20 mL). An aqueous solution of NaOH (10 eq., 40 mL) was added and the reaction mixture was heated at 60° C. for three hours. The methanol was removed in vacuo and the remaining reaction mixture was cooled to 0° C. and concentrated HCl was added drop wise until the pH reached 2-3. The aqueous solution was extracted with DCM, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound.

후처리

  1. customThe methanol was removed in vacuo
  2. customthe remaining reaction mixture
  3. temperaturewas cooled to 0° C.
  4. extractionThe aqueous solution was extracted with DCM
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8713304cdd2f4b50856f140ef5d8c8af
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183381B2

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