Methanol → HCID 46244492, compound

HRID 1803848Notes

Reaction equation

HRID 1803848 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[Cl:26])=[CH:14][CH:15]=2)[C:10]([NH:27][C:28](=[O:55])[C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[CH:31][C:30]=2[N:42]([CH:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)C(=O)C(F)(F)F)=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[Cl:26][C:20]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=1[CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][N:9]=[C:10]2[NH:27][C:28](=[O:55])[C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]2)=[CH:31][C:30]=1[NH:42][CH:49]1[CH2:50][CH2:51][O:52][CH2:53][CH2:54]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 86761740HCID 86761740, compound

Product 1

HCID 46244492HCID 46244492, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2-Chloro-5-fluoro-benzyloxy)-3-{4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-indazole-1-carboxylic acid tert-butyl ester (100 mg, 0.1269 mmol) in DCM (1.3 mL) was treated at room temperature with TFA (0.195 mL, 2.538 mmol). After 2 hours the volatiles were evaporated and the residue was treated with MeOH (3 mL) and TEA (0.357 mL, 2.538 mmol) and refluxed for three hours. After evaporation of the volatile components the crude was diluted with DCM (25 mL), washed with water, aqueous NaHCO3, water and finally brine, dried over sodium sulfate, evaporated and purified by flash chromatography over silica gel (eluent: DCM:7N NH3 in MeOH 93:7) to give 40 mg of title compound.

Workup

  1. customAfter 2 hours the volatiles were evaporated
  2. temperaturerefluxed for three hours
  3. customAfter evaporation of the volatile components the crude
  4. additionwas diluted with DCM (25 mL)
  5. washwashed with water, aqueous NaHCO3, water and finally brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. custompurified by flash chromatography over silica gel (eluent: DCM:7N NH3 in MeOH 93:7)

Sources & evidence

ORD record
ord-b15fe902e04045dc8c52ed6409f68928
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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