Maleic Acid → N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-trans-2-phenylcyclopropane-1-carboxamide, dimaleate salt

HRID 432420노트

반응식

HRID 432420 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:31]3[CH2:36][CH2:35][N:34]([CH:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)[CH2:33][CH2:32]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C@@H:20]4[CH2:22][C@H:21]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:19])=[C:13]([O:29][CH3:30])[CH:12]=3)[C:3]=12.[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48]>C(O)C>[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[C:44]([OH:51])(=[O:50])/[CH:45]=[CH:46]\[C:47]([OH:49])=[O:48].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:31]3[CH2:32][CH2:33][N:34]([CH:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)[CH2:35][CH2:36]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C@@H:20]4[CH2:22][C@H:21]4[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:19])=[C:13]([O:29][CH3:30])[CH:12]=3)[C:3]=12

참가 물질

4

반응물 2

HCID 444266Maleic AcidHCID 20817142N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-trans-2-phenylcyclopropane-1-carboxamide

생성물 1

HCID 131724252N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-trans-2-phenylcyclopropane-1-carboxamide, dimaleate salt수율 71.5%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

N1-{4-[4-Amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-trans-2-phenylcyclopropane-1-carboxamide (75 mg, 0.129 mmol) was dissolved in ethanol (2 mL) and maleic acid (45 mg, 0.387 mmol) in ethanol (1 mL) was added. The reaction mixture was stirred at room temperature for 5 hours. The solvent was removed and ethyl acetate was added and the solid was collected by filtration to give N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-trans-2-phenylcyclopropane-1-carboxamide, dimaleate salt (75 mg). 1H NMR (DMSO-d6) δ 1.17 (m, 1H), 1.32 (m, 2H), 1.48 (m, 2H), 1.48, (m, 2H), 2.19 (m, 4H), 2.37 (M, 1H), 2.46 (m, 1H), 2.59 (m, 1H), 2.78 (s, 3H), 2.98-3.52 (bm, 9H), 3.90 (s, 3H), 5.02 (m, 1H), 6.08 (s, 4H), 7.17-7.33 (m, 7H), 8.25 (m, 2H), 9.65 (s, 1H). LCMS (Finigan-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 3.0 mL/min.): MH+ =581.4, Rt=1.77 min.

후처리

  1. customThe solvent was removed
  2. additionethyl acetate was added
  3. filtrationthe solid was collected by filtration

출처 및 근거

ORD 기록
ord-84fa890f35454977a25ffa8489ac8ddb
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

반응 노트

불러오는 중…