Hydrochloric Acid → 4-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid

HRID 1506099

반응식

HRID 1506099 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:13][C:14]3[N:15]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])[C:16](=[O:25])[C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[N:9]=[C:10]([CH:11]=[O:12])[C:3]=12.[O-]Cl=O.[Na+].Cl.[NH2:38][C:39]1[N:44]=[CH:43][N:42]=[C:41]2[N:45]([CH2:51][C:52]3[N:53]([C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=4[CH3:70])[C:54](=[O:63])[C:55]4[C:60]([CH:61]=3)=[CH:59][CH:58]=[CH:57][C:56]=4[CH3:62])[N:46]=[C:47]([C:48]([OH:50])=[O:49])[C:40]=12>CC(O)(C)C.O.CCC=CC>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:13][C:14]3[N:15]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])[C:16](=[O:25])[C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:24])[N:9]=[C:10]([C:11]([NH2:38])=[O:12])[C:3]=12.[NH2:38][C:39]1[N:44]=[CH:43][N:42]=[C:41]2[N:45]([CH2:51][C:52]3[N:53]([C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=4[CH3:70])[C:54](=[O:63])[C:55]4[C:60]([CH:61]=3)=[CH:59][CH:58]=[CH:57][C:56]=4[CH3:62])[N:46]=[C:47]([C:48]([OH:50])=[O:49])[C:40]=12

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 23668197Sodium ChloriteHCID 580085994-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carbaldehyde2회HCID 580088444-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid

생성물 2

HCID 580085964-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamideHCID 580088444-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid수율 47%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6386tert-Butanol용매HCID 12585Pent-2-ene용매

실험 절차

To a stirred solution of 4-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carbaldehyde (compound 4502) (400 mg, 0.94 mmol) in t-BuOH (1.8 mL), a solution of NaH2PO4 (3.90 g, 28.27 mmol) in water (4.8 mL), methyl-2-butene (1.0 mL) and (dropwise) a solution of NaClO2 (767 mg, 6.78 mmol) in water (4.8 mL) were added sequentially. The mixture was stirred at RT for 3 h under an argon atmosphere. The pale yellow solution was acidified with aqueous HCl solution (2 M, 4 mL) to PH=2 and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was triturated with anhydrous ethyl ether and ethyl acetate. The solid was collected by filtration to afford the desired product, 4-amino-1-((8-methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid (compound 4601) (200 mg, 47% yield) as a yellow solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with anhydrous ethyl ether and ethyl acetate
  7. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-67ad8c01e187479abb7a9cb2bd2908ad
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216982B2

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