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

HRID 218480

반응식

HRID 218480 반응식
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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 249594685-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl ester

생성물 1

HCID 249594695-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid수율 93%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  1. temperatureAfter cooling to rt
  2. customAfter the removal of MeOH
  3. customthe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-6ff1eeceae73415380a6197ce477547c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

연결된 노트

불러오는 중…