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Sodium Hydroxide → 1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid

HRID 1410009
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HRID 1410009 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:30]=[CH:29][S:28][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([O:26]C)=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>C1COCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:30]=[CH:29][S:28][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([OH:26])=[O:25])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 68379218Methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylate

생성물 1

HCID 683795141-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid수율 98.7%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a stirred solution of methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylate (0.06 g, 0.139 mmol) in 5 mL of THF and 5 mL of methanol was added a solution of NaOH (0.056 g, 1.39 mmol) in 1 mL of water at room temperature. After the addition, the reaction was stirred at this temperature for 24 hours. The solvent was evaporated and the residue was suspended in 10 mL of THF, then treated by HCl until pH=2. The solvent was evaporated and then dissolved in 30 mL of THF, filtered. The filtrate was evaporated to give 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (0.057 g, 98%) as a solid. LC-MS: 416.1 [M+H]+, tR=1.57 min.

후처리

  1. additionAfter the addition
  2. customThe solvent was evaporated
  3. additiontreated by HCl until pH=2
  4. customThe solvent was evaporated
  5. dissolutiondissolved in 30 mL of THF
  6. filtrationfiltered
  7. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-37091756db514c7ca9e34352e0e96e70
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921383B2

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