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Potassium Carbonate → N-(3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)-6-{[2-(4-morpholinyl)ethyl]oxy}-3-pyridinecarboxamide

HRID 1986407
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HRID 1986407 반응식
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[NH2:11][C:12]1[C:13]([C:17]2[N:18]([CH2:43][CH3:44])[C:19]3[CH:24]=[C:23]([O:25][C:26]4[CH:27]=[C:28]([NH:32][C:33]([C:35]5[CH:40]=[CH:39][C:38](=[O:41])[NH:37][CH:36]=5)=[O:34])[CH:29]=[CH:30][CH:31]=4)[N:22]=[CH:21][C:20]=3[N:42]=2)=[N:14][O:15][N:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[NH2:11][C:12]1[C:13]([C:17]2[N:18]([CH2:43][CH3:44])[C:19]3[CH:24]=[C:23]([O:25][C:26]4[CH:27]=[C:28]([NH:32][C:33]([C:35]5[CH:36]=[N:37][C:38]([O:41][CH2:3][CH2:4][N:5]6[CH2:10][CH2:9][O:8][CH2:7][CH2:6]6)=[CH:39][CH:40]=5)=[O:34])[CH:29]=[CH:30][CH:31]=4)[N:22]=[CH:21][C:20]=3[N:42]=2)=[N:14][O:15][N:16]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 68875466HCID 68875466, 화합물

생성물 1

HCID 57721180N-(3-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)-6-{[2-(4-morpholinyl)ethyl]oxy}-3-pyridinecarboxamide수율 30%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

2-Chloroethylmorpholine hydrochloride (104 mg, 0.6 mmol) was added to a slurry of the product of Step 2 (135 mg, 0.3 mmol) and powdered K2CO3 (1 g) in DMF (2 mL) and the mixture was heated to 80° C. for 3 h. The mixture was cooled, diluted with H2O and extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried (MgSO4), filtered and the filtrate was concentrated to give a yellow oil which was purified by reverse phase HPLC to give the title compound (50 mg, 30%). 1H NMR (400 MHz, CD3OD) δ ppm 9.13 (s, 1H), 8.69 (s, 1H), 8.09 (d, J=9.3, 1H); 7.92 (s, 1H), 7.69 (d, J=8.0, 1H), 7.60-7.53 (m, 2H), 7.12 (d, J=8.0, 1H), 6.67 (d, J=9.4, 1H), 4.76 (br q, 2H), 4.53 (br m, 2H), 3.83-3.70 (m, 8H), 3.33 (m, 2H), 1.46 (br t, 3H). MS (ES+) m/e 572 [M+H]+.

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give a yellow oil which
  8. customwas purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-31ccd9d8523b4771ae7749092b647ff7
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07547779B2

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