Potassium Hydroxide → 3-(3-Tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid

HRID 221882

반응식

HRID 221882 반응식
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:14]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=4)=[CH:21][C:20]=3[F:33])=[O:17])=[CH:13][C:12]([C:34]([CH3:37])([CH3:36])[CH3:35])=[N:11]2)[CH:5]=1.COC(=O)C1C=CC(N2C(NC(NC3C=CC(OC4C=CN=C(C)C=4)=CC=3F)=O)=CC(C(C)(C)C)=N2)=CC=1.[OH-].[K+]>CO.O>[C:34]([C:12]1[CH:13]=[C:14]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=3)=[CH:21][C:20]=2[F:33])=[O:17])[N:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:38])=[O:2])[N:11]=1)([CH3:37])([CH3:35])[CH3:36]

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 536301844-(3-Tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid methyl esterHCID 536301873-(3-Tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid methyl ester

생성물 1

HCID 536301863-(3-Tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid수율 98%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

To a solution of 3-(3-tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid methyl ester (2.0 g, 4.12 mmol; prepared in a similar manner as described for 4-(3-tert-butyl-5-{3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzoic acid methyl ester) in methanol, was added potassium hydroxide (692 mg, 12.4 mmol) in water. The mixture was stirred at 40° C. overnight, then cooled to room temperature. Methanol was evaporated at reduced pressure, and the aqueous residue neutralized to pH 7 by addition of 2N HCl. The white solid that formed was collected by filtration and dried in vacuo to give the title compound (1.9 g, 98%). 1H-NMR (DMSO-d6) δ 8.95 (s, 1H), 8.92 (s, 1H), 8.30 (d, J=5.7 Hz, 1H), 8.11-8.03 (m, 2H), 7.94 (d, 10.2 Hz, 1H), 7.79 (d, J=9.9 Hz, 1H), 7.65 (t, J=7.5 Hz, 1H), 7.18 (J=14.1 Hz, 1H), 6.95 (d, J=12.9 Hz, 1H), 6.75 (m, 2H), 6.39 (s, 1H), 2.39 (s, 3H), 1.89 (s, 9H); MS LC-MS [M+H]+=504.2, RT=2.47 min.

후처리

  1. customprepared in a similar manner
  2. temperaturecooled to room temperature
  3. customMethanol was evaporated at reduced pressure
  4. additionthe aqueous residue neutralized to pH 7 by addition of 2N HCl
  5. customThe white solid that formed
  6. filtrationwas collected by filtration
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-6ca1ed9273c34dd1812738959e23766b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207166B2

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