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1,1'-Carbonyldiimidazole → 1-[(2-isopropoxy-6-methyl-3-pyridyl)methyl]-3-(3-oxo-4H-1,4-benzoxazin-8-yl)urea

HRID 1505229
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HRID 1505229 반응식
[CH:1]([O:4][C:5]1[C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=[C:7]([CH3:13])[N:6]=1)([CH3:3])[CH3:2].C1N=CN([C:19](N2C=NC=C2)=[O:20])C=1.[NH2:26][C:27]1[C:32]2[O:33][CH2:34][C:35](=[O:37])[NH:36][C:31]=2[CH:30]=[CH:29][CH:28]=1>C1COCC1.CN(C=O)C>[CH:1]([O:4][C:5]1[C:10]([CH2:11][NH:12][C:19]([NH:26][C:27]2[C:32]3[O:33][CH2:34][C:35](=[O:37])[NH:36][C:31]=3[CH:30]=[CH:29][CH:28]=2)=[O:20])=[CH:9][CH:8]=[C:7]([CH3:13])[N:6]=1)([CH3:3])[CH3:2]
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참가 물질

6

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HCID 682631,1'-CarbonyldiimidazoleHCID 115934888-Amino-2H-1,4-benzoxazin-3(4H)-oneHCID 61655597[2-Isopropoxy-6-methyl-3-pyridyl]methanamine

생성물 1

HCID 534767031-[(2-isopropoxy-6-methyl-3-pyridyl)methyl]-3-(3-oxo-4H-1,4-benzoxazin-8-yl)urea수율 21%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8028
Tetrahydrofuran
용매

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온도
70 °C

실험 절차

To a solution of 33a (1.14 g, 6.35 mmol) in THF (30 mL) was added CDI (2.1 mol eq, 2.16 g) and the mixture was heated at 70° C. for 6 h. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×35 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (yellow oil, 1.61 g, 93% yield). The oil obtained (0.34 g, 1.25 mmol) was dissolved in DMF (20 mL) and the bicyclic amine 1f was added (0.8 mol eq, 0.20 g), then the mixture obtained was heated at 100° C. overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (1:1 EtOAc:Petroleum ether) to obtain the product as a white solid (0.07 g, 21% Yield). 1HNMR (DMSO, 400 MHz) δ 1.28 (s, 3H), 1.31 (s, 3H), 2.34 (s, 3H), 4.14 (d, 2H, J=6), 4.60 (s, 2H), 5.25 (m, 1H), 6.48 (dd, 1H), 6.77 (m, 2H), 7.11 (t, 1H), 7.44 (d, 1H, J=8), 7.71 (dd, 1H), 8.16 (s, 1H), 10.64 (bs, 1H). [M+1] 370.95 (C19H22N4O4 requires 370.40).

후처리

  1. customThe reaction mixture was evaporated
  2. additionwater was added
  3. extractionthe aqueous phase was extracted with EtOAc (3×35 mL)
  4. customevaporated at reduced pressure (yellow oil, 1.61 g, 93% yield)
  5. customThe oil obtained (0.34 g, 1.25 mmol)
  6. custom0.20 g), then the mixture obtained
  7. temperaturewas heated at 100° C. overnight
  8. customThe solvent was removed at reduced pressure
  9. customthe residue was purified by chromatography (1:1 EtOAc:Petroleum ether)

출처 및 근거

ORD 기록
ord-40a52ea9dd24487d84cdeb0824231b30
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09216975B2

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