Lithium Hydroxide → 4-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid

HRID 605351노트

반응식

HRID 605351 반응식
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([NH:18][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[N:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:5]=1.[Li+].[OH-]>C1COCC1>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([S:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][C:6]=2[NH:18][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[N:25][C:21]=3[N:22]=[CH:23][N:24]=2)=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 3939Lithium Hydroxide2회HCID 670402984-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester

생성물 1

HCID 670409154-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid수율 73.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 4-(4-hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester (0.50 g, 1.1 mmol) in THF (5 mL) was added aqueous LiOH [prepared from LiOH monohydrate (0.15 g) and H2O (1.5 mL)] dropwise at room temperature. The mixture was stirred at room temperature for 24 hours. Additional aqueous LiOH [prepared from LiOH monohydrate (0.15 g) and H2O (1.5 mL)] was added at room temperature. The mixture was mixture was stirred at room temperature for 23 hours, and then evaporated. The aqueous mixture was diluted with 50 mL of H2O, washed with AcOEt, and treated with active charcoal. The mixture was filtered and the filtrate was carefully acidified to pH 4-5 with 10% HCl under stirring. The resulting solid was collected by filtration, washed with H2O, and dried at 40° C. for 3 days under reduced pressure to give the title compound as pale yellow crystal (0.35 g, 73%). 1H-NMR (300 MHz, DMSO-d6) δ ppm: 1.33 (d, J=7.0 Hz, 6H), 3.22 (septet, J=7.0 Hz, 1H), 6.81-6.90 (m, 1H), 6.85 (d, J=8.5 Hz, 2H), 7.30 (d, J=8.5 Hz, 2H), 7.63 (br-d, J=8.4 Hz, 1H), 7.73 (br-d, J=8.1 Hz, 1H), 7.85 (br-s, 1H), 8.57 (s, 1H), 8.86 (d, J=8.4 Hz, 1H), 10.14 (s, 1H).

후처리

  1. stirringwas stirred at room temperature for 23 hours
  2. customevaporated
  3. additionThe aqueous mixture was diluted with 50 mL of H2O
  4. washwashed with AcOEt
  5. additiontreated with active charcoal
  6. filtrationThe mixture was filtered
  7. stirringunder stirring
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with H2O
  10. customdried at 40° C. for 3 days under reduced pressure

출처 및 근거

ORD 기록
ord-990980f6bb5b4948bd235a6f5ec2a99c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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