Trifluoroacetic acid → HCID 59577332, compound

HRID 1186613Notes

Reaction equation

HRID 1186613 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[C:45]([F:47])[CH:46]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:31][CH2:32][CH:33]1[CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]1)=[O:17].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:35]1[CH2:34][CH:33]([CH2:32][NH:31][C:19]2[CH:20]=[C:21]([N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)[CH:22]=[CH:23][C:18]=2[C:16]([NH:15][C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][C:4]4[CH:3]=[C:2]([F:1])[CH:46]=[C:45]([F:47])[CH:44]=4)[CH:7]=3)[NH:11][N:10]=2)=[O:17])[CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68672281HCID 68672281, compound

Product 1

HCID 59577332HCID 59577332, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-butyl 3-({[2-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-5-(4-methylpiperazin-1-yl)phenyl]amino}methyl)azetidine-1-carboxylate (289 mg, 0.45 mmol) was dissolved in DCM (3 mL) and TFA (0.7 mL) was added. The resulting reaction solution was stirred overnight at room temperature. The mixture was diluted with DCM and extracted with 10% acqueous NH3. Organic phase was evaporated. Reverse phase column chromatography purification afforded 104 mg of the title compound.

Workup

  1. customThe resulting reaction solution
  2. extractionextracted with 10% acqueous NH3
  3. customOrganic phase was evaporated
  4. customReverse phase column chromatography purification

Sources & evidence

ORD record
ord-6a616158e2a54bf080a396a91755f511
Source dataset
uspto-grants-2014_03
Patent number
US08673893B2

Reaction notes

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