Triethylamine → [(2-Amino-5-bromo-pyridin-3-ylmethyl)ethoxycarbonylmethyl-amino]acetic acid ethyl ester

HRID 1362056

반응식

HRID 1362056 반응식
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.[NH:12]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C>CC#N>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:12]([CH2:10][C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([Br:2])[CH:4]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:18]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 80502Diethyl iminodiacetateHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

생성물 1

HCID 59456979[(2-Amino-5-bromo-pyridin-3-ylmethyl)ethoxycarbonylmethyl-amino]acetic acid ethyl ester수율 51%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (12.0 g, 34.6 mmol) and diethyl iminodiacetate (7.0 mL, 39.1 mmol) in CH3CN (350 mL) was treated with triethylamine (10.7 mL, 76.1 mmol). After stirring at room temperature under N2 for 4 h, the solvent was removed in vacuo. The resulting yellow slurry was partitioned between H2O (400 mL) and EtOAc (400 mL), and the aqueous layer was extracted with EtOAc (200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1) gave the title compound (6.55 g, 51%) as a light tan oil: MS (ESI) m/e 374 (M+H)+.

후처리

  1. customthe solvent was removed in vacuo
  2. customThe resulting yellow slurry was partitioned between H2O (400 mL) and EtOAc (400 mL)
  3. extractionthe aqueous layer was extracted with EtOAc (200 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1)

출처 및 근거

ORD 기록
ord-366cd80ac872488d80edf53025b8836b
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

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