Hydrochloric Acid → 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid

HRID 218480

反応式

C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]3[C:19]([C:20]#[N:21])=[C:18]([CH3:22])[NH:17][C:16]([CH3:23])=[C:15]3[C:24]#[N:25])[CH:12]=2)[NH:7][N:6]=1)=[O:4].[Li+].[OH-].Cl>CO.O>[C:20]([C:19]1[CH:14]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][N:6]=[C:5]3[C:3]([OH:4])=[O:2])[C:15]([C:24]#[N:25])=[C:16]([CH3:23])[NH:17][C:18]=1[CH3:22])#[N:21]

参加物

反応条件

温度: 70 °C

実験手順

To 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl ester (110 mg, 0.33 mmol) in MeOH—H2O (1:1, 8 mL) was added LiOH (1.08 g, 26.4 mmol) at rt. The reaction mixture was heated up to 70° C. for 2 days. After cooling to rt, the solution was acidified to pH 7 with 1 N HCl. After the removal of MeOH, the residue was purified by HPLC to afford 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid (98 mg, 93%) (Cpd. No. 86, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=8.04 (s, 1H), 7.78 (s, 1H), 7.41 (d, 1H), 4.62 (s, 1H), 2.1 (s, 6H) ppm.

後処理

temperatureAfter cooling to rt
customAfter the removal of MeOH
customthe residue was purified by HPLC

出典と根拠

ORDレコード: ord-6ff1eeceae73415380a6197ce477547c
出典データセット: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08198456B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート