Acetic Acid → N-(5-bromothiazol-2-yl)-cyclopropylmethylamine

HRID 1670536노트

반응식

HRID 1670536 반응식
C(O)(=O)C.[Br:5][C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1>C(Cl)Cl>[Br:5][C:6]1[S:10][C:9]([NH:11][CH2:29][CH:26]2[CH2:28][CH2:27]2)=[N:8][CH:7]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 436002-Thiazolamine, 5-bromo-HCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 59822318N-(5-bromothiazol-2-yl)-cyclopropylmethylamine수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Add acetic acid (2 mL, 33.4 mmol) to a mixture of 5-bromo-thiazol-2-ylamine (1 g, 5.6 mmol), sodium triacetoxyborohydride (3.5 g, 16.7 mmol) and cyclopropane carboxaldehyde (820 mg, 11.7 mmol) at room temperature under a nitrogen atmosphere. Stir the resulting solution for 1.5 h at ambient temperature. Dilute the solution with DCM (50 mL) and wash with saturated aqueous NaHCO3 (80 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (9:1 to 7:3 gradient) to obtain the title compound (970 mg, 75%). MS (ES+) m/z: 233.1 (M+).

후처리

  1. washwash with saturated aqueous NaHCO3 (80 mL)
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by chromatography on silica gel (40 g)
  6. washeluting with hexane/EtOAc (9:1 to 7:3 gradient)

출처 및 근거

ORD 기록
ord-f3187df32cfd4517987610280afe49d7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994163B2

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