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Sodium Hydroxide → 2-[8-(1,3-Benzothiazol-2-Ylcarbamoyl)-3,4-Dihydroisoquinolin-2(1h)-Yl]-5-{3-[4-(1h-Pyrazolo[3,4-D]pyrimidin-1-Yl)phenoxy]propyl}-1,3-Thiazole-4-Carboxylic Acid

HRID 1518283
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HRID 1518283 반응식
[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:5]2=[N:6][CH:7]=[N:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[H-].[Na+].[S:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[NH:28][C:29]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[CH2:39][N:38]([C:41]1[S:42][C:43]([CH2:51][CH2:52][CH2:53]I)=[C:44]([C:46]([O:48]CC)=[O:47])[N:45]=1)[CH2:37][CH2:36]2)=[O:30].[OH-].[Na+]>CN(C=O)C.CO.C1COCC1>[N:1]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:53][CH2:52][CH2:51][C:43]3[S:42][C:41]([N:38]4[CH2:37][CH2:36][C:35]5[C:40](=[C:31]([C:29](=[O:30])[NH:28][C:20]6[S:19][C:23]7[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=7[N:21]=6)[CH:32]=[CH:33][CH:34]=5)[CH2:39]4)=[N:45][C:44]=3[C:46]([OH:48])=[O:47])=[CH:14][CH:15]=2)[C:5]2=[N:6][CH:7]=[N:8][CH:9]=[C:4]2[CH:3]=[N:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 594187194-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenolHCID 59447467ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylate

생성물 1

HCID 468368622-[8-(1,3-Benzothiazol-2-Ylcarbamoyl)-3,4-Dihydroisoquinolin-2(1h)-Yl]-5-{3-[4-(1h-Pyrazolo[3,4-D]pyrimidin-1-Yl)phenoxy]propyl}-1,3-Thiazole-4-Carboxylic Acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of compound 21D (106 mg, 0.498 mmol) in DMF (5 mL) was added sodium hydride (56.9 mg, 1.423 mmol). The resulting mixture was stirred at rt for 30 minutes and compound 2C (300 mg, 0.474 mmol) was added. The reaction mixture was stirred for 1 hour and 10% sodium hydroxide (1.897 mL, 4.74 mmol), THF (5 mL) and MeOH (3 mL) was added. The resulting mixture was stirred at 70° C. overnight, cooled, and filtered. The filtrate was acidified by HCl to pH 4. The precipitate was collected and dried to provide the desired product: 1H NMR (400 MHz, DMSO-D6) δ ppm 12.85 (1H, s), 9.45 (1H, s), 9.10 (1H, s), 8.61 (1H, s), 7.98-8.06 (3H, m), 7.78 (1H, d), 7.67 (1H, d), 7.42-7.50 (2H, m), 7.32-7.40 (2H, m), 7.09-7.16 (2H, m), 4.84 (2H, s), 4.06 (2H, t), 3.73 (2H, t), 3.14-3.24 (2H, m), 3.03 (2H, t), 1.98-2.12 (2H, m); LCMS (APCI): m/z 687 (M+H).

후처리

  1. stirringThe reaction mixture was stirred for 1 hour
  2. stirringThe resulting mixture was stirred at 70° C. overnight
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe precipitate was collected
  6. customdried

출처 및 근거

ORD 기록
ord-43972c3fd67a4c289d390319e516c3b6
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232273B2

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