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

反応式

HRID 1506099 の反応式
[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

参加物

9

反応物 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-carbaldehyde2 回HCID 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

生成物 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 acid収率 47%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 12585Pent-2-ene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-67ad8c01e187479abb7a9cb2bd2908ad
出典データセット
uspto-grants-2015_12
特許番号
US09216982B2

関連ノート

読み込み中…