Water → Methyl 8-(benzyloxy)-5-(6-(tert-butoxycarbonylamino)hexylamino)-1,6-naphthyridine-7-carboxylate

HRID 455304노트

반응식

HRID 455304 반응식
[CH2:1]([O:8][C:9]1[C:10]([C:20]([O:22][CH3:23])=[O:21])=[N:11][C:12](Br)=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44].O>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([C:20]([O:22][CH3:23])=[O:21])=[N:11][C:12]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:47])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2733170N-BOC-1,6-diaminohexaneHCID 71699854Methyl 8-(benzyloxy)-5-bromo-1,6-naphthyridine-7-carboxylate

생성물 1

HCID 68009435Methyl 8-(benzyloxy)-5-(6-(tert-butoxycarbonylamino)hexylamino)-1,6-naphthyridine-7-carboxylate

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

Methyl 8-(benzyloxy)-5-bromo-1,6-naphthyridine-7-carboxylate (Example 1; 5.50 g; 14.7 mmol) was dissolved in DMA (300 ml). DIPEA (5.14 ml; 29.5 mmol) was added at room temperature. The reaction mixture was stirred for 5 min at room temperature. tert-Butyl 6-aminohexylcarbamate (4.95 ml; 22.1 mmol) was added and the reaction mixture was stirred at 100° C. for 12 hours. The reaction mixture was cooled. Water and ethyl acetate were added. The organic layer was separated and washed with water (×2) and with brine. The organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: hexane/EtOAc from 10:1 to 1:1). The product fractions were collected and the solvent evaporated.

후처리

  1. stirringthe reaction mixture was stirred at 100° C. for 12 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. washwashed with water (×2) and with brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by flash column chromatography over silica gel (eluent: hexane/EtOAc from 10:1 to 1:1)
  9. customThe product fractions were collected
  10. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-1b720af5b0eb436785a1229e391c5f2b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497270B2

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