Hydrochloric Acid → 3-(2-(4-aminopiperidin-1-yl)pyrimidin-4-yl)-N,N-dimethyl-1H-indazole-5-carboxamide

HRID 1529446노트

반응식

HRID 1529446 반응식
[CH3:1][N:2]([CH3:40])[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10](C1CCCCO1)[N:9]=[C:8]2[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([N:26]2[CH2:31][CH2:30][CH:29]([NH:32]C(=O)OC(C)(C)C)[CH2:28][CH2:27]2)[N:21]=1)=[O:4].Cl>CCOC(C)=O>[NH2:32][CH:29]1[CH2:30][CH2:31][N:26]([C:22]2[N:21]=[C:20]([C:8]3[C:7]4[C:11](=[CH:12][CH:13]=[C:5]([C:3]([N:2]([CH3:40])[CH3:1])=[O:4])[CH:6]=4)[NH:10][N:9]=3)[CH:25]=[CH:24][N:23]=2)[CH2:27][CH2:28]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86709796tert-butyl (1-(4-(5-(dimethylcarbamoyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrimidin-2-yl)piperidin-4-yl)carbamate

생성물 1

HCID 679767933-(2-(4-aminopiperidin-1-yl)pyrimidin-4-yl)-N,N-dimethyl-1H-indazole-5-carboxamide수율 56.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl (1-(4-(5-(dimethylcarbamoyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrimidin-2-yl)piperidin-4-yl)carbamate (0.4 g, 0.728 mmol) in EtOAc (8 mL) was added HCl (4 N in dioxane, 8 mL) and the reaction was stirred at RT for 3 h The mixture was quenched with water and neutralized with NaHCO3 and extracted with EtOAc. The organic layer was separated and dried over Na2SO4, filtered and concentrated. The residue was purified with HPLC (5-50% MeCN in water with 0.1% TFA) to give 3-(2-(4-aminopiperidin-1-yl)pyrimidin-4-yl)-N,N-dimethyl-1H-indazole-5-carboxamide (150 mg, 52%) as an off white solid. MS (ESI, pos. ion) m/z: 366.2 (M+1); 1H NMR (300 MHz, DMSO-d6): −δ 13.88 (s, 1H), 8.53 (s, 1H), 8.48 (d, 2 H, J=5.1 Hz), 7.96 (s, 3H), 7.70 (d, 1 H, J=8.6 Hz), 7.52 (dd, 1 H, J=8.6, 1.4 Hz), 7.38 (d, 1 H, J=5.1 Hz), 4.77 (d, 2 H, J=13.6 Hz), 3.41 (bs, 1H), 3.09-3.20 (m, 2H), 3.03 (s, 6H), 2.03 (d, 2 H, J=10.5 Hz), 1.47-1.58 (m, 2H).

후처리

  1. customwas quenched with water and neutralized with NaHCO3
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with HPLC (5-50% MeCN in water with 0.1% TFA)

출처 및 근거

ORD 기록
ord-52a59c7361604ea6851f837386fdeab4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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