Sodium hydride → 2-Phenyl-ethanesulfonic acid {5-p-tolyl-6-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-amide

HRID 8617

반응식

HRID 8617 반응식
[H-].[Na+].[OH:3][CH2:4][CH2:5][O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][S:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:16])=[O:15])[C:8]=1[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.Cl[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=1>C1COCC1>[C:28]1([CH3:31])[CH:29]=[CH:30][C:25]([C:8]2[C:9]([NH:13][S:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:15])=[O:16])=[N:10][CH:11]=[N:12][C:7]=2[O:6][CH2:5][CH2:4][O:3][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=2)=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 235482692-Phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

생성물 1

HCID 235482452-Phenyl-ethanesulfonic acid {5-p-tolyl-6-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-amide수율 88.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To sodium hydride (27 mg, 60% in mineral oil) was added THF (15 ml) followed by 2-phenyl-ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (80 mg, Referential Example 1). The mixture was stirred for 1 h at rt before 2-chloro-5-trifluoromethyl-pyridine (86 mg) was added. Stirring was continued for 17 h at 80° C. The solvent was evaporated, the residue was dissolved in water (20 ml), acidified with citric acid. The suspension was treated with hexane (15 ml). The solid material was collected, washed with hexane:EA 1:1 (20 ml) and dried to yield 2-phenyl-ethanesulfonic acid {5-p-tolyl-6-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-amide (96 mg) as beige powder. LC-MS: tR=5.86 min, [M+1]+=559.20, [M−1]−=557.37.

후처리

  1. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in water (20 ml)
  4. additionThe suspension was treated with hexane (15 ml)
  5. customThe solid material was collected
  6. washwashed with hexane:EA 1:1 (20 ml)
  7. customdried

출처 및 근거

ORD 기록
ord-7ba9c64b1ade4f3bbbe979f0ff322f01
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091201B2

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