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Methanol → tert-butyl 3-{[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl]amino}propylcarbamate

HRID 1784477
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HRID 1784477 반응식
CS(O[CH:6]([C:9]1[N:10]=[C:11]2[CH2:26][CH2:25][CH2:24][CH2:23][N:12]2[C:13](=[O:22])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7][CH3:8])(=O)=O.[NH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].[I-].[K+].CO>CN(C=O)C.C(Cl)Cl>[NH3:10].[CH2:15]([C:14]1[C:13](=[O:22])[N:12]2[CH2:23][CH2:24][CH2:25][CH2:26][C:11]2=[N:10][C:9]=1[CH:6]([NH:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:7][CH3:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

8

반응물 4

HCID 887MethanolHCID 4875Potassium IodideHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 575932061-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl methanesulfonate

생성물 2

HCID 222Ammonia수율 0.1%
HCID 57593203
tert-butyl 3-{[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl]amino}propylcarbamate
수율 28.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

A mixture of 0.106 g (0.28 mmol) of the product from Step 9 (25), 0.15 g (0.84 mmol) of tert-butyl 3-aminopropylcarbamate, and 0.005 g (0.03 mmol) of potassium iodide in 5 mL of DMF was stirred at 60° C. under nitrogen for 24 hours. The reaction was quenched with water, extracted with ethyl acetate (4×) and the combined organic layers were washed with saturated NaHCO3 and brine and dried over MgSO4. The solvent was removed in vacuo and the crude reaction mixture was subjected to flash chromatography on a 7 cm column. Elution with a gradient of 50% ethyl acetate in hexanes, 100% ethyl acetate, 3% methanol and 0.1% ammonia in DCM, and 10% methanol and 0.1% ammonia in DCM yielded 0.019 g (0.04 mmol, 15%) of tert-butyl 3-{[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl]amino}propylcarbamate (26) as a clear oil.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (4×)
  3. washthe combined organic layers were washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customthe crude reaction mixture
  7. washElution with a gradient of 50% ethyl acetate in hexanes, 100% ethyl acetate, 3% methanol and 0.1% ammonia in DCM

출처 및 근거

ORD 기록
ord-42dac9e0cc2e438baefdc9be2c640253
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07504405B2

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