Ethyl Acetate → HCID 66769520, 화합물

HRID 1472588

반응식

HRID 1472588 반응식
[Cl:1][C:2]1[C:3]([NH:18][C:19]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23]C=2C#N)=[CH:4][C:5]([NH:8][C:9]2[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[C:11]([CH3:17])[CH:10]=2)=[N:6][CH:7]=1.[OH-].[Na+].[C:30]([O:33]CC)(=[O:32])[CH3:31]>O1CCOCC1>[Cl:1][C:2]1[C:3]([NH:18][C:19]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:31]=2[C:30]([OH:33])=[O:32])=[CH:4][C:5]([NH:8][C:9]2[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[C:11]([CH3:17])[CH:10]=2)=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 667697122-[(5-Chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluorobenzonitrile

생성물 1

HCID 66769520HCID 66769520, 화합물수율 75%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluorobenzonitrile (4.5 g, 11.69 mmol) in sodium hydroxide—1 M (10 mL, 10.00 mmol) and 1,4-dioxane (10 mL) was refluxed overnight. Ethyl acetate was added and the layers were separated. The organic layer was washed with 1 M NaOH (40 ml). Combined aqueous layers were washed with ethyl acetate, and neutralized with acetic acid. The solid was filtered. 2-[(5-Chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluorobenzoic acid (3.2 g, 7.53 mmol, 75% yield) was isolated as a yellow solid. 1H NMR (400 MHz, DMSO-d6) ppm 1.24 (d, J=6.57 Hz, 6 H) 2.09 (s, 3 H) 4.34 (quin, J=6.57 Hz, 1 H) 5.86 (s, 1 H) 5.91 (d, J=5.81 Hz, 1 H) 7.35 (td, J=8.02, 4.93 Hz, 1 H) 7.54-7.65 (m, 1 H) 7.81 (d, J=7.58 Hz, 1 H) 7.94 (s, 1 H) 8.45 (s, 1 H) 8.88 (br. s., 1 H) 13.74 (br. s., 1 H); HPLC Rt=2.36 min, MS (ESI): 404.3 [M+H]+.

후처리

  1. customthe layers were separated
  2. washThe organic layer was washed with 1 M NaOH (40 ml)
  3. washCombined aqueous layers were washed with ethyl acetate
  4. filtrationThe solid was filtered

출처 및 근거

ORD 기록
ord-86f38fb4aec04bfe8cccc5a0e85bda52
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012479B2

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