Cesium carbonate → (NZ)-N-[3-(4-methylsulfanylphenyl)-1,3-thiazol-2-ylidene]pyrrolidine-1-carboxamide

HRID 390711

반응식

HRID 390711 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8].ClC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:36]1[CH:41]=[CH:40][C:39]([S:42][CH3:43])=[CH:38][CH:37]=1.[OH-].[NH4+].O>CN1CCCC1=O>[CH3:43][S:42][C:39]1[CH:40]=[CH:41][C:36]([N:3]2[CH:4]=[CH:5][S:1]/[C:2]/2=[N:6]\[C:7]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:8])=[CH:37][CH:38]=1

참가 물질

7

반응물 5

HCID 10796Cesium carbonateHCID 660374-BromothioanisoleHCID 778655-Chloro-1,10-phenanthrolineHCID 86589665Water ammonium hydroxideHCID 86631924N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide

생성물 1

HCID 42644655(NZ)-N-[3-(4-methylsulfanylphenyl)-1,3-thiazol-2-ylidene]pyrrolidine-1-carboxamide

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

In a 4 mL vial charged with a stir bar, N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide (53 mg, 0.27 mmol, Example 32A) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (27 mg, 0.05 mmol), 5-chloro-1,10-phenanthroline (23 mg, 0.11 mmol) and cesium carbonate (97 mg, 0.3 mmol). A loose cap with a septum was placed on the vial, and then the vial was placed under vacuum in a vacuum oven for 30 minutes. The mixture was purged with nitrogen gas a couple of times. Then (4-bromophenyl)(methyl)sulfane (61 mg, 0.3 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the solid mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then a 1 mL solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid).

후처리

  1. additionIn a 4 mL vial charged with a stir bar
  2. customA loose cap with a septum
  3. customThe mixture was purged with nitrogen gas a couple of times
  4. additionwas added to the solid mixture
  5. customThe vial was capped
  6. customplaced on a heater/stirrer
  7. filtrationThe reaction was filtered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-41024ed908ea4d54b1693ca2cb354739
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383657B2

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