Cyclohexanecarboxaldehyde → HCID 21865115, compound

HRID 859044Notes

Reaction equation

HRID 859044 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[N:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=4[NH2:28])[CH:13]=3)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:29]1([CH:35]=O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C([O-])(O)=O.[Na+].O>[CH:29]1([CH2:35][NH:28][C:19]2[CH:20]=[C:21]([C:24]([F:25])([F:27])[F:26])[CH:22]=[CH:23][C:18]=2[C:14]2[CH:13]=[C:12]([O:11][C:8]3[CH:9]=[C:10]4[C:5]([CH:4]=[CH:3][CH:2]=[N:1]4)=[CH:6][CH:7]=3)[N:17]=[CH:16][N:15]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10474988HCID 10474988, compound

Product 1

HCID 21865115HCID 21865115, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenylamine, (Example 163), (0.40 g, 1.1 mmol) in 1,2-dichloroethane (11 mL) was added cyclohexanecarboxaldehyde (0.32 mL, 2.6 mmol, Aldrich) and the mixture was stirred at room temperature for 18 h. NaBH(OAc)3 (0.55 g, 2.6 mmol) was added and stirring was continued for 8 h at 40° C. The reaction was diluted with satd NaHCO3 and H2O, and extracted with EtOAc (2×75 mL). The combined extracts were washed with H2O (75 mL) and brine (75 mL), dried over Na2SO4, filtered and concentrated onto silica gel. Purification by silica gel chromatography (gradient, 10 to 40% EtOAc/hexanes) afforded the title compound as a yellow solid. Mp: 137–138° C. MS (ESI, pos. ion) m/z: 479.2 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued for 8 h at 40° C
  3. extractionextracted with EtOAc (2×75 mL)
  4. washThe combined extracts were washed with H2O (75 mL) and brine (75 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated onto silica gel
  8. customPurification by silica gel chromatography (gradient, 10 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-77714c02cabe44669b8a7f53aa56a0af
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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