Hydrochloric Acid → HCID 69915157, 화합물

HRID 402492

반응식

HRID 402492 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][C:16]([O:21][CH2:22][C:23](O)=[O:24])=[CH:17][C:18]=3[CH3:20])[N:13]([CH3:26])[N:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CCN(CC)CC.[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([C@@H:53]([NH2:55])[CH3:54])=[CH:49][CH:48]=1>C(Cl)Cl.O.C(Cl)CCl>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][C:16]([O:21][CH2:22][C:23]([NH:55][C@H:53]([C:50]4[CH:51]=[CH:52][C:47]([O:46][CH3:45])=[CH:48][CH:49]=4)[CH3:54])=[O:24])=[CH:17][C:18]=3[CH3:20])[N:13]([CH3:26])[N:12]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 793467(S)-1-(4-Methoxyphenyl)ethylamineHCID 67209308HCID 67209308, 화합물

생성물 1

HCID 69915157HCID 69915157, 화합물수율 12.4%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of [3-(3,5-Dimethoxy-phenyl)-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy]-acetic acid (building block A1, 100 mg, 0.28 mmol) in CH2Cl2 were added HOBt×H2O (64 mg, 0.42 mmol), EDC×HCl (80 mg, 0.42 mmol) and NEt3 (0.12 ml, 0.84 mmol). After stirring at rt for 5 min, (S)-1-(4-methoxyphenyl)ethanamine (64 mg, 0.42 mmol) was added and stirring continued for 18 h. Then, water was added and the mixture extracted 3 times with DCM. The organic phases were dried over Na2SO4 and the solvent removed under reduced pressure. Purification by reverse phase HPLC (Sunfire C18 OBD column) followed by liberation of the free base (SPE cartridge SCX-1, eluent 7M NH3 in methanol) yielded the title compound (17 mg, 12%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.48 (d, 1H), 7.21 (d, 2H), 6.82 (d, 2H), 6.70 (s, 1H), 6.58 (s, 1H), 5.00-4.88 (m, 1H), 4.87 (d, 1H), 4.83 (d, 1H), 3.85 (s, 3H), 3.78 (s, 6H), 3.70 (s, 3H), 2.37 (s, 3H), 1.37 (d, 3H); UPLC-MS RtJ=1.14 min; [M+H]+=491.2]

후처리

  1. stirringstirring
  2. waitcontinued for 18 h
  3. extractionthe mixture extracted 3 times with DCM
  4. dry with materialThe organic phases were dried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. customPurification by reverse phase HPLC (Sunfire C18 OBD column)

출처 및 근거

ORD 기록
ord-e6dcf59335d04c8181b79a90a5b7843a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742106B2

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