Triethylamine → Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoate

HRID 911869

반응식

HRID 911869 반응식
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[Br:11][C:12]1[CH:13]=[C:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]([NH:18][C:19]([NH2:21])=[S:20])=[N:16][CH:17]=1.C(N(CC)CC)C>C(O)C>[Br:11][C:12]1[CH:13]=[C:14]([O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:15]([NH:18][C:19]2[S:20][CH:2]=[C:3]([CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[N:21]=2)=[N:16][CH:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9855825Methyl 5-bromo-4-oxopentanoateHCID 866314811-(5-Bromo-3-phenoxypyridin-2-yl)thiourea

생성물 1

HCID 86631509Methyl 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanoate수율 80.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of methyl 5-bromo-4-oxopentanoate (2.51 g, 12.0 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (3.00 g, 9.25 mmol), triethylamine (2.19 mL, 15.7 mmol), and ethanol (60 mL) was refluxed for 3 hours and then stirred at ambient temperature overnight. The solvent was removed to about one third original volume and partitioned between CH2Cl2 and water. The organics were concentrated and purified on silica gel eluting with 40% EtOAc/Hexanes to give the title compound (3.22 g, 80.1% yield).

후처리

  1. temperaturewas refluxed for 3 hours
  2. customThe solvent was removed to about one third original volume
  3. custompartitioned between CH2Cl2 and water
  4. concentrationThe organics were concentrated
  5. custompurified on silica gel eluting with 40% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-16cb3420468b41fc98fb55df90cecb09
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022223B2

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