Triethylamine → 1-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1H-indazol-5-yl]-amide

HRID 1037986Notes

Reaction equation

HRID 1037986 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[O:18]=[C:19]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41]3[N:46]=[CH:45][CH:44]=[CH:43][N:42]=3)=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)[CH2:20][N:21]1[CH2:25][CH2:24][CH:23]([C:26](O)=[O:27])[CH2:22]1.C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:26]([CH:23]4[CH2:24][CH2:25][N:21]([CH2:20][C:19](=[O:18])[N:29]5[CH2:30][CH2:31][N:32]([C:35]6[CH:40]=[CH:39][C:38]([C:41]7[N:42]=[CH:43][CH:44]=[CH:45][N:46]=7)=[CH:37][CH:36]=6)[CH2:33][CH2:34]5)[CH2:22]4)=[O:27])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 224802843-(4-fluorophenyl)-1H-indazol-5-amineHCID 674194121-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid2×

Product 1

HCID 674186161-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1H-indazol-5-yl]-amideYield 24.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Fluoro-phenyl)-1H-indazol-5-ylamine (0.11 gm, 0.5 mmol) and 1-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid (compound 12 from Step 9, 0.125 gm, 0.25 mmol) were dissolved in 4 ml of DMF. O-(7-azabenzotriazol-1-yl-)-N,N,N,N-tetramethyluronium hexafluorophosphate (HATU) (0.24 gm, 0.63 mmol) and triethylamine (0.1 ml, 0.76 mmol) were added to the reaction mixture and the mixture stirred for 18 hrs. The reaction mixture was added to bring and extracted with dichloromethane. After drying over magnesium sulfate and filtered, the mixture was evaporated and chromatographed to obtain 36.7 mg of title product.

Workup

  1. additionThe reaction mixture was added
  2. extractionextracted with dichloromethane
  3. dry with materialAfter drying over magnesium sulfate
  4. filtrationfiltered
  5. customthe mixture was evaporated
  6. customchromatographed

Sources & evidence

ORD record
ord-28a69d1d9e274c4eb35d0d6333e45324
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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