2-(cyclohexylmethyl)-5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one → HCID 178480053、化合物

HRID 2241311ノート

反応式

HRID 2241311 の反応式
[CH:1]1([CH2:7][C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]5[N:29](CC6C=CC(OC)=CC=6)[N:30]=[C:31]([C:32]6[CH:37]=[CH:36][C:35]([C:38]([N:40]7[CH2:45][CH2:44][O:43][CH2:42][CH2:41]7)=[O:39])=[CH:34][CH:33]=6)[C:24]=45)=[C:18]([F:55])[CH:17]=3)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[CH:1]1([CH2:7][C:8]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]5[NH:29][N:30]=[C:31]([C:32]6[CH:37]=[CH:36][C:35]([C:38]([N:40]7[CH2:45][CH2:44][O:43][CH2:42][CH2:41]7)=[O:39])=[CH:34][CH:33]=6)[C:24]=45)=[C:18]([F:55])[CH:17]=3)=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

3

反応物 1

HCID 685153872-(cyclohexylmethyl)-5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one

生成物 1

HCID 178480053HCID 178480053、化合物

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of 2-(cyclohexylmethyl)-5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one (0.027 g, 0.0363 mmol) in TFA (1 mL) was stirred at 60° C. for 3 minutes and then at ambient temperature overnight. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and saturated NaHCO3. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined EtOAc layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 10:1 CH2Cl2/MeOH. The product was obtained (17.3 mg; 76%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (d, 1H), 8.27 (s, 1H), 8.08 (d, 2H), 7.89 (m, 1H), 7.71 (m, 1H), 7.59-7.49 (m, 4H), 6.43 (d, 1H), 3.60 (m, 8H), 3.53 (s, 3H), 2.73 (d, 2H), 1.96 (m, 1H), 1.82-1.59 (m, 5H), 1.34-0.99 (m, 5H). LRMS (APCI pos) m/e 623 (M+1).

後処理

  1. customat ambient temperature
  2. customovernight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was partitioned between EtOAc and saturated NaHCO3
  5. customThe layers were separated
  6. extractionthe aqueous layer was re-extracted with EtOAc (1×)
  7. dry with materialThe combined EtOAc layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash column chromatography
  11. washeluting with 10:1 CH2Cl2/MeOH
  12. customThe product was obtained (17.3 mg; 76%) as a yellow solid

出典と根拠

ORDレコード
ord-6ef142709c1a4962915b188279328261
出典データセット
uspto-grants-2010_05
特許番号
US07723330B2

反応ノート

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