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Ethyl bromoacetate → HCID 67335596, 화합물

HRID 1672158
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HRID 1672158 반응식
[NH2:1][CH2:2][C:3]1([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[CH:13]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].CCN(CC)CC>C1COCC1>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH:1][CH2:2][C:3]1([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[CH:13]3)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)[CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 67335147HCID 67335147, 화합물

생성물 1

HCID 67335596HCID 67335596, 화합물수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (1-aminomethyl-cyclohexyl)-(1H-indazol-5-yl)-amine (0.775 g, 3.18 mmol) in THF (7 mL) at 0° C. under nitrogen was added ethylbromoacetate (0.530 g, 0.351 mL, 3.18 mmol) and Et3N (1.42 mL, 10.2 mmol) then the reaction mixture warmed to room temperature. After 90 minutes the mixture was concentrated in vacuo then redissolved in DCM (100 mL) and washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered and concentrated in vacuo to an oil (1.4 g). Purification by chromatography (silica, 0 to 10% of a 9:1 MeOH:NH4OH solution in DCM) gave {[1-(1H-indazol-5-ylamino)-cyclohexylmethyl]-amino}-acetic acid ethyl ester (0.877 g, 2.66 mmol, 84%) as a solid.

후처리

  1. concentrationAfter 90 minutes the mixture was concentrated in vacuo
  2. dissolutionthen redissolved in DCM (100 mL)
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil (1.4 g)
  7. customPurification by chromatography (silica, 0 to 10% of a 9:1 MeOH:NH4OH solution in DCM)

출처 및 근거

ORD 기록
ord-419f376c2bbd41908b6191ca8515e3cf
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07998963B2

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