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, compound

HRID 2241311Notes

Reaction equation

HRID 2241311 reaction equation
[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

Participants

3

Reactant 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

Product 1

HCID 178480053HCID 178480053, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6ef142709c1a4962915b188279328261
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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