Trifluoroacetic acid → HCID 10142929, compound

HRID 2109640Notes

Reaction equation

HRID 2109640 reaction equation
Cl[C:2]1[N:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:8]=1)=[O:5].[NH2:30][C:31]1[CH:39]=[C:38]2[C:34]([CH:35]=[N:36][NH:37]2)=[CH:33][CH:32]=1.C(O)(C(F)(F)F)=O>Cl>[NH:37]1[C:38]2[C:34](=[CH:33][CH:32]=[C:31]([NH:30][C:2]3[N:29]=[CH:28][CH:27]=[CH:26][C:3]=3[C:4]([NH:6][C:7]3[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([CH2:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:8]=3)=[O:5])[CH:39]=2)[CH:35]=[N:36]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 814231H-Indazol-6-amineHCID 219595982-Chloro-N-[3-[3-(4-morpholinyl)propyl]-5-(trifluoromethyl)phenyl]-3-pyridinecarboxamide

Product 1

HCID 10142929HCID 10142929, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
155 °C

Procedure

2-Chloro-N-[3-(3-morpholin-4-yl-propyl)-5-trifluoromethyl-phenyl]-nicotinamide (2.95 g) was dissolved in a small volume of IpOH. 6-amino indazole (2.75 g) and 0.53 mL of TFA were added. The reaction mixture was heated to 155° C. in an open flask for 3.5 h. After cooling to RT the residue was dissolved in 2 N HCl. The aqueous solution was extracted 2 times with CH2Cl2, basified to pH 12 by the addition of Na2CO3 and 1 N NaOH. The solution was extracted 6 times with CH2Cl2 to isolate the product. The combined 5 extractions were dried over Na2SO4, filtered and stripped. The crude product was purified by silica gel chromatography eluting with a step gradient of 3-5% MeOH:CH2Cl2 to yield the titled compound. MS: 525 (M+1). Calc'd for C27H27F3N6O2-524.5.

Workup

  1. temperatureAfter cooling to RT the residue
  2. extractionThe aqueous solution was extracted 2 times with CH2Cl2
  3. additionbasified to pH 12 by the addition of Na2CO3 and 1 N NaOH
  4. extractionThe solution was extracted 6 times with CH2Cl2
  5. customto isolate the product
  6. extraction5 extractions
  7. dry with materialwere dried over Na2SO4
  8. filtrationfiltered
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a step gradient of 3-5% MeOH

Sources & evidence

ORD record
ord-4fe8638b9db449768809e815449f830d
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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